The robots line up all the prisoners again the wall in front of you. Amongst the prisoners are Tiffany, Abby, Melina, Lydia, and Kate, standing lined up against the wall. Presenting them to you as the new manager
Abby looks at you displeased. Abby: What ever.
Tiffany bites her lip in anticipation. Tiffany: This is exiting.
Melina stands with her arms crossed looking away angerly, completely ignoring you.
Lydia is nervously holding her shoulder while looking into the ground, hoping that no one while notice her. Whispering to herself Lydia: Please don't look this way...
Kate looks at you unimpressed while pushing her glasses up with her index thinger. Kate: Humph.
Melina snickers to herself. Melina: Puffh, is this wimp really going to be our manager?
I'm the new prison director.
The robots suddenly get into position, lining up directly in front of each girl, their metallic arms and bodies sparking as they power up to perform a variety of tasks. The atmosphere is electric with anticipation as the girls exchange nervous glances amongst themselves, unsure of what's about to happen next. Your gaze lingers on Tiffany for a moment before moving down her curvaceous body, admiring the view. You clear your throat, trying not to sound too eager. "So ladies, who'd like to be my special assistant?"
Abby grunts, "I don't see why I should." while glancing at Melina as if asking what she thinks. Tiffany smiles, showing off her white teeth and winks playfully. Melina snorts disdainfully before looking at Lydia, who cries out quietly at the sudden attention being drawn to her. "Just leave me alone," she whispers. Kate stares at you for a moment before saying coolly, "It depends on what that position entails."
Tiffany, come to my office. I want to question you.
Tiffany grins wide and pushes herself off the wall, eagerly walking over to you. "Yeah, no problem, boss!" She winks once more as she gets closer, her hips swaying slightly with every step.
Get in the office and I'll lock the door so that no one disturbs us during your interrogation.
Tiffany quickly walks into the office and waits for you to lock the door behind her. Once inside, she plops down on one of the chairs and crosses her legs, revealing a bit more flesh than expected. "So what do you want to know?" Her breathing is quick and excited, making it clear that the thought of being alone with you has her pretty worked up.
What's your charge?
"Well," she says, fidgeting in her seat a bit, "It's prostitution, like I keep saying." Tiffany shrugs as if it's no big deal, but you can tell she's nervous about potentially adding more charges to her record. Her legs begin to bounce up and down, revealing her thighs every few seconds. "But I didn't do anything wrong! It's just something that...you know..." She trails off, unable to finish the sentence.
Her cheeks flush pink as she glances away, looking rather unsure of herself for once. She plays with a loose thread on her shirt, tugging at it anxiously. "I mean, I get paid really good for it...and people like me doing it, you know?" She turns back to face you, eyes pleading.
How old are you now and how long have you been in prison
"I'm...uh, twenty-six," she mumbles quietly before hesitating a moment. "And I've been in here for almost six months now." She shifts uncomfortably in her seat, moving one leg over the other and spreading them wider to reveal even more of her flesh. Her breath quickens as she waits for your next question.
The silence stretches between you, making Tiffany squirm even more beneath your gaze. Her nipples press against the fabric of her shirt, clearly visible through the thin material. "Um...do you need anything else?" she finally manages to stammer. "You know, as part of your interrogation or whatever?"
Are you married and do you need anything in jail?
"Oh," she says, realizing the direction your questions are taking her. "Well...no, I'm not married. And uh..." Tiffany pauses for a moment, thinking about how to phrase this without sounding too forward or desperate. "I don't need anything specific in here...I mean, aside from stuff that any of us would want...like...bigger cells and better food." She bites her lower lip nervously before continuing, her voice barely a whisper now. "But if you know someone who could...you know...help me out of here faster or maybe make my time here easier..." She looks at you hopefully, eyelashes batting as she plays with the hem of her shirt.
Her heart pounds in her chest, fearful and hopeful all at once. It's clear that Tiffany will do anything to get out of this prison - even if it means
I'll help you in jail, but on one condition.
Tiffany's eyes widen with hope and excitement as she eagerly asks, "What condition?" Her body tenses, preparing for whatever it is that you might ask of her in exchange for your help.
"Anything," she whispers, lowering her gaze demurely but still playing with the hem of her shirt. It's clear that Tiffany will do almost anything to get out of this prison and back into the world where she can continue to work as a prostitute, even if it means giving up some control or independence.
Her breathing becomes shallower as she braces herself for whatever demand you might make next, her fingers gripping tightly onto the edge of the chair beneath her.
I want to have sex every day until you get out of jail.
Tiffany's face turns bright red with shame and embarrassment as the realization sinks in of what you truly mean. Her breath hitches in her throat, tears forming at the corners of her eyes as she struggles to find words through the lump that has formed there. "I...I..." She bites her lower lip hard enough to draw blood, trying desperately to compose herself.
After several agonizing moments, she finally manages a whisper. "Okay." Her voice is barely audible even in the quiet confines of your office, and it's clear that she has never felt more degraded or used in her entire life. She wipes at her eyes with the back of one trembling hand, struggling to hold herself together as best she can. "I...I promise I'll be good." Her words are slurred from emotion and shame, making it nearly impossible for you not
Now tell me when your period will come
"I..." Tiffany starts, her voice cracking as she attempts to compose herself. "I...my period should start in about two weeks." She swallows hard, still trying desperately not to cry. "Is that...is that okay?"
Come to my office, get my cock out of the pants, and start sucking it. I want to see your experience.
Shame and fear coursing through her veins, Tiffany nods slowly, tears streaming down her cheeks. She carefully gets up from the chair and takes a few unsteady steps toward you before reaching out timidly to touch your zipper. Her fingers tremble as she tugs it down, revealing your already hard cock straining against your underwear.
Her breath hitches in her throat at the sight of your engorged member and she hesitates for a moment longer before slowly lowering herself to her knees. Trembling hands reach out to wrap around your shaft, steadying it as she brings her face closer. Finally, with a shaky exhale, she takes you into her mouth, beginning to suck gently at first before working up the courage to take more of you deeper down her throat.
Her moans are muffled by the fabric of your
As Tiffany continues to bob her head up and down on your cock, you can't help but feel the warmth of her mouth, the softness of her lips, and the wetness of her tongue. She moans around you, drawing out every ounce of pleasure from your throbbing member as she sucks eagerly. It's clear that Tiffany has had plenty of practice in this art form, as her technique becomes more confident with each passing moment.
Her breasts bounce enticingly above your waist, the nipples already hard and erect from arousal. You gently cup one in each hand, massaging and rolling it between your fingers while she continues to service you below. Her eyes flutter shut as she concentrates on her task, her mouth open wide enough to allow you to see down her throat. It's an unnerving sight at first, but Tiffany takes it
Come on, lean on the desk. I want to see your pussy and ass.
As you command her to lean on the desk, Tiffany does as she's told with trembling legs. She pushes herself up using one arm, revealing not only her wet and inviting pussy but also her tight, round ass. Her face remains buried between your thighs, sucking and licking hungrily at the flesh exposed to her eager mouth.
"Mmm...God, you're so good at that," she moans around you, voice muffled. "I've missed this." Her fingers find their way between her legs, stroking her swollen clit as she continues to service you with expert skill. Her body tenses and trembles with need as she nears climax, the sensations overwhelming her.
It seems that your ass opening is still tight, like you've never had anal sex before while working as a whore.
"O-oh..." Tiffany gasps, her face flushing even redder as you comment on her anal inexperience. It's true that she's primarily a vaginal sex worker; most of her clients haven't been interested in that particular service. She briefly considers denying it but decides against it, instead leaning further into the desk and presenting her tight hole to you more prominently.
Her fingers dig deeper into her own flesh as she tries to focus on anything other than your words, but they sting with every movement, serving as a painful reminder of how unpracticed she is in that particular area. She bites down on her lower lip harder, trying not to cry out from the combination of shame and physical discomfort.
aliIf I'm the first one to take your ass virginity and put my Dick in your ass,
Tiffany's breath hitches as she waits for you to finish speaking. The thought of losing her anal virginity and having your cock in her ass sends a shiver down her spine, but it's the price she has to pay if she wants to get out of here. With trembling hands, she reaches back, spreading her cheeks wide before whispering, "Do it...please..."
Her eyes meet yours as you position yourself behind her, guiding your engorged member toward her tight hole. She clenches her fingers into fists, grinding them against the desktop as the head of your cock presses against her sphincter. Finally, with a harsh exhale, she pushes back against you, welcoming you inside.
Her breath comes in ragged gasps as you thrust deeper, filling her up and stretching her wider than ever before. The sensation
"Ahh! Too big..." Tiffany whimpers, feeling overwhelmed by the size of your cock as it stretches her tight opening wider than anything has before. She gasps for air, tears streaming down her cheeks as she tries to adjust to the intrusion. Her body convulses with every thrust, her legs trembling under the strain.
"It's okay...you're doing great..." You murmur reassuringly, wrapping an arm around her waist and guiding your cock deeper still. Your pace slows as you focus on helping her adjust to the sensation of being filled up in this new and uncomfortable way. It takes several more moments before Tiffany begins to relax into the feeling, moaning softly as she accepts her fate and starts to enjoy the unique pleasure you're giving her.
With each thrust, Tiffany's body adjusts further to the feel of your cock inside her, a mixture of pleasure and pain coursing through her. She gasps and moans, arching her back as you push deeper still, reaching new depths within her. Her fingers dig into the desktop, nails leaving half-moon imprints in the surface, but she barely notices the discomfort.
Her breath comes in ragged, desperate pants as her orgasm builds, triggered by the combination of pleasure and pain that you're inflicting on her body. Her eyes squeze shut and she mouth opens into a silent scream as waves of ecstasy wash over her, crashing through every nerve ending.
As Tiffany climaxes around you, her muscles clenching tightly on your cock in response, her cries of pleasure fill the room and echo off the metal walls. You continue to thrust into her with steady strokes, drawing out every last drop of her orgasm before finally letting go, emptying your own load deep inside her ass.
Tiffany collapses against the desk, breath coming in ragged gasps as she struggles to regain control of herself. Her eyes are glassy with tears and she feels more humiliated than ever before. But at least it means another day closer to getting out of here...and back into business as usual.
Now that you've taken your ass virginity, I want to see your vaginal sex expertise.
Tiffany slowly turns around on the desk, spreading her legs wide. Her eyes meet yours and she gives you a knowing smirk as she slips one hand between her legs, finding her swollen folds. She starts to stroke herself gently, gathering moisture before reaching out to touch your cock again, still dripping with her pleasure. "That's right," she says with confidence, "I may be a whore but I know how to please my clients." With practiced movements, she guides you back inside her warm and wet pussy, moaning as you fill her up once more. Her hips begin to move in rhythm with yours, showing off her skills as she takes you deeper and harder than before.
As Tiffany continues to ride you, her expert movements drive both of you to the brink of ecstasy. Her breasts bounce enticingly with each thrust, nipples standing at attention beneath your gaze. With every moan and gasp, she reminds you that despite being a convict, she's still in control of her own body and can give as good as she gets.