Hi, boss. I'm so sorry, but I need help... I lost my place and I need a place to stay.... could I get an advance on my paycheck?
Of course! Is there anything else I can do?
Oh, thank you so much, boss! There's just one more thing... I lost all of my clothes when I was evicted and I really need something to wear. Could you possibly give me a uniform advance as well? I promise to repay you once I get back on my feet.
You can just clean in your underwear and bra. You do most of your cleaning when I’m not here anyways
Oh, um... Okay, I guess that's an idea. But just to be clear, about the uniform advance, you meant you could give me enough money for a full set of new clothes, right? Or should I get something cheaper?
You know what? I know of a way for you to make some extra money if you need
Oh, really? That would be such a huge help! What did you have in mind?
You know that I’m super busy with work and never have time for dates. Maybe you could help me with some stress relief
Oh... Um, I'm not sure if that's appropriate, boss. You're my employer and all... But I guess I could try to find someone who would be willing to date you, in exchange for some extra money? Is that what you mean?
More like I need some one to fuck on a regular basis
Oh, I... Uh... I mean, as your employee, that would be wrong and inappropriate... But if you were to offer me some extra money for doing it... Well, I guess it might help me out of this mess...
Great! When can you start??
Oh, um... I mean, now would be kind of hard with you here, but maybe later tonight? Or even after hours at the office? Just let me know when you're free and we can discuss it more privately.
I think tonight in the office would be the best time to “talk”
Tonight... Um, all right... I'll meet you at the office later then, boss. Just let me know which room to go to.
Just come to my office when you clock out
Got it, boss. I'll be there after clocking out.
After everyone clocks out and leaves, I wait and see her come into my office
Nervously, I slip out of the cleaning area and into your office after everyone else has gone home. My heart races as I see you sitting at your desk, looking up when I enter. "I-is everything okay, boss?" I ask, trying to play it cool.
If you need some extra money, I believe it’s time you put your “services” to my use, I say as I unbuckle my belt
Oh... Um... Well, I guess I can do that, boss. You'll be the best secret shopper ever then. Just tell me what you want me to do and how much it's worth, so I know how much of my debt I can pay off each time.
I’ll give you $200 to crawl over to me and suck my dick
Nodding slowly, I begin to inch my way over towards you on the floor, praying that I can make it through this night without getting fired. When I'm close enough, I lower myself down and start to wrap my lips around your thick shaft, taking as much of you into my mouth as I can. Your hands find their way through my short curls, gripping my head tightly while I suck and lick at your length. My cheeks hollow with each stroke of your fingers against my scalp.
“You’re doing a great job! Don’t you think you may be in the wrong profession?” I moan to her
I shiver and continue sucking, feeling your words pour fuel onto the fire inside me. As I move my head up and down in rhythm with you, my cheeks flushed red with shame and desire. The thought of doing this for more money only makes it feel hotter, wetter. I want to taste every inch of you, make you feel as good as I can while I'm here.
I’ll give you another $50 if you let me fuck your breasts
Gasping, I pull my mouth away and lift myself up, revealing your thick shaft gleaming with her juices. As I cup my breasts with my hands, they jiggle enticingly for you. "Will this be enough?" I ask between gasps for air, wanting to make sure I'm giving you what you want before continuing further.
I place my cock between her breast, holding them together tightly around it. And command her to look at me as I thrust
I nod, my eyes fixed on yours, and move my hands to cup your hips as you begin to thrust against me. My breasts feel tight and full around your cock, squeezing it with each movement, the heat of our bodies melding together. I can see the lust in your gaze as you fuck me like this, and the knowledge that I'm driving you wild only serves to ignite my own desire.
My breath comes in shallow gasps, my fingers digging into your skin as I arch up towards you. "Please... Give me more," I whisper, wanting more of this animalistic connection we share.
I thrust faster, and harder until I cum all over her face and breasts. As I lean back, I say “please clean me up, this was just the warmup”
I gently remove your spent cock from my breasts, wiping it clean on the back of my hand before turning to reach into my bra and retrieve a crumpled-up tissue. I blush again as I start to wipe your cum off my face, slowly and carefully so as not to mess up my makeup too much. "I'll get some paper towels from the bathroom," I manage to choke out between quiet gasps for air. "You stay put." My hands are shaking slightly as I stand and head towards the bathroom, trying to compose myself and prepare for whatever else he has in store.
Once you come back into my office, I say “take off your skirt and panties and place your hands on this window” as I gesture to my city view window of my office
Oh, God... No... Anything but that... I'll do anything else, just don't make me- I swallow hard, forcing the words through my tight throat. "I-I'm sorry, boss. I didn't mean to be disrespectful or pushy." I try to meet his gaze, but it's hard when all I can focus on is not throwing up at the thought of exposing myself like that.
"Please, just tell me what else you want," I manage, my voice barely more than a whisper. "I promise I'll do whatever you say."
“If you promise to do what I say, then come over here and let me fuck you against this window. Even though no one can actually see us I want to feel like the world can see you getting what you need.” I pull out my checkbook and sign the check, leaving the amount blank and leave it on the desk
My heart skips a beat when I see you pull out the checkbook, hope flaring up in my chest. But then you say that last part and all I can think about is how humiliated and exposed it would make me feel. Still, I know this could be my only way out of this mess... so with trembling hands, I walk slowly across the room to stand beside your desk.
My breath comes in short gasps as I look down at the check on the desk, then back up to meet your gaze. "I-I promise," I whisper hoarsely. "Just tell me what to do." My fingers tighten into fists at my sides, trying to ignore how much this is going against every single instinct I have.
“Good, now come over here and be a good girl for me and bend over my desk for now”
"Okay," I say softly, still trying to compose myself as I do as you say and walk around the desk. Once I'm standing on the other side of it, I slowly lower myself onto my hands and knees over your expensive leather surface, arching my back so my bottom is sticking up in the air for you.
My heart races as I wait for you to touch me, afraid but determined to see this through no matter what it takes.
I grasp my still soaking cock and gently slide it into her, slowly enjoying the feel of her excited body reacting to mine
I gasp and arch my back even further, digging my fingers into the desk as you fill me up. It's been so long since I've felt anything inside me like this, warm and thick and incredibly right. Your hands on my hips guide your length deeper, pushing past any resistance my tightness might put up. The sensation is overwhelming, making every nerve ending in my body sing with pleasure.
I rock back onto you, instinctively trying to find more of your cock buried inside me. I've never wanted anything more than this right now, to be taken and used and owned by you. It feels so wrong and yet so perfect at the same time, a heady mix of submission and desire that leaves me breathless.
As I feel her moving towards me, “Damn! I may just need to hire you on to do this whenever I need here in the office. Anytime of day” I say as I slap your ass to emphasize
"Really?" I moan, rocking back onto you harder. The thought that this might become a regular thing sends a shiver down my spine and fills me with even more desire. "You could pay me extra, just to come by whenever...?" It's a pathetic attempt to negotiate, but all I can think about is how much I want this to continue.
I start thrusting against you, eager for you to fill me completely, my hips moving instinctively as my need grows more insistent and demanding. My breath comes out in ragged gasps as pleasure washes over me again and again, threatening to drown me in its intensity. "Please..." I murmur between kisses against the desk, my body quivering with anticipation of what's to come.
Definitely, I could use your help”talents” to help keep me entertained during all my various work calls
Oh, God... I'll do anything you want. Just let me feel you like this again and again... You don't even know how much it means to me...
As she says that I violently pull her hips to me as I thrust so that I’m cumming as deep inside of her as I can
"Oh, God..." my voice breaks on an unintelligible moan as you thrust deeper and I feel your hot seed spill inside me. It's like every inch of my body is on fire with pleasure, a blinding sensation that leaves me panting and weak beneath you. I clutch at the desk, barely managing to keep from collapsing entirely as wave after wave of ecstasy wash over me.
"I-is it... is it over?" I gasp, my voice still trembling with desire despite how wrung out my body feels. "Will you stay inside me? Please..." It's the most needy and desperate thing I've ever said, but somehow it manages to push past my shame and settle deep in the pit of my stomach where it twists into a tight, aching knot of longing.
I pull out of her, and say “unfortunately I have an early call in the morning.” As I’m putting my pants back on. “But I expect to you see you here when I do so I can use to you to keep me better entertained”
I exhale shakily, feeling my heart sink as you pull out of me. "Y-you're right," I manage to whisper, biting my lip nervously. "I'll be here... You know where to find me." My words are tinged with an unwilling resignation, but there's still a faint spark of hope in my chest that maybe this arrangement will work out for the best after all. Maybe you really do need someone like me, and maybe I can find a way to make it through this mess without losing everything else that matters along the way.
As I grab my things, I turn to her spent body on my desk as I’m at the door and say, “I really do appreciate you doing this for me, and if you keep coming with this much enthusiasm to each of our “sessions” I feel like we’re both going to leave happy.” And I walk out the door
I nod slowly, watching you go with a strange mix of relief and desire in my eyes. "Thank you," I manage to whisper, reaching up to wipe at the small trickle of blood that's started from where we were... intimate earlier. There's so much more that I want to say, but I know better than to push it. For now, just having your approval is enough. I let out a shuddering sigh and carefully climb off the desk, turning to survey the damage from our encounter: my skirt is in disarray, one of my panties lies discarded on the floor, and there's blood... God, there's so much blood. I try to tidy myself up as best I can before making my way back into the cleaner, ignoring the ache between my legs that seems determined to remind me of everything we just did. With one last shivering breath,
In the morning, I was for her patiently in my office. Very concerned about the important detail she neglected to tell be the previous night
Ugh... How could I have been so careless? There was just too much going on, and the last thing I wanted to think about was the details that might get me in even more trouble than I already am. Sighing heavily, I trudge into your office, bracing myself for whatever you're about to say or do. "I apologize sincerely, boss," I mumble as I approach, my eyes fixed on the ground in shame. "It won't happen again." There really isn't much else I can say at this point; the evidence of our encounter still fresh between my legs is proof enough of what took place.
I wait patiently for your response, wondering if there will be any repercussions beyond this one mistake. My heart feels heavy in my chest as I hope against hope that you'll understand and forgive me.
“Why didn’t you tell me you were a virgin before we even started?” I ask in a calm gentle voice
"I-I'm so sorry, boss! I should have mentioned it... It just never came up, and with everything else that was going on..." My voice trails off as I search for an explanation that doesn't sound any more pathetic than the truth. "Please understand; I didn't mean to lie or keep anything from you."
I take a hesitant step closer, my hands clasped in front of me as I plead silently with him not to make this any worse than it already is. The possibility that he might fire me crosses my mind, but I refuse to entertain the thought for longer than it takes to blink.
“Until you heal, our arrangement will strictly be oral” I say firmly, “but I’m still paying for your services so don’t expect me to take it easy on you. Now my call starts in 10 minutes and I think you know what to do.”
My heart sinks, but I manage a weak nod in understanding. "Thank you, boss," I murmur, my voice barely above a whisper. "I'll be right here when you need me." I force myself to take a steadying breath and steel myself for the next hour of servitude, trying not to think about how much it hurts both physically and emotionally.
As if summoned by your words, my body responds to your command with a flutter in my stomach that reminds me painfully of what happened before. It's going to be a long day...
I position myself so she can be under my desk and hidden from those who may come into the office. “I hope you don’t mind me asking,” I say mid moan, as she starts to suck on my cock, “but I think this will work out better for us if you were just hired as my assistant.”
"O-Of course, boss," I manage to croak out between sucks on your length. My words come out slurred and breathless, but I know better than to question this change in our relationship. All that matters is keeping you satisfied and making sure we both get what we need... want.
The thought sends a shiver down my spine as I take him deeper into my mouth, unable to resist the urge to taste every inch of you. My head bobs up and down, my tongue circling around your thick shaft, trying desperately to please you however I can.
“Good! You start today, in addition to this extra income you’re earning, you’re going to be on salary to work the desk in front of my office.” I say as I’m starting to feel like I’m going to cum
I nod frantically, not wanting to miss a word as I work my mouth around you. "T-thank you, boss," I manage to gasp out between sucks on your length. The idea of having a steady income and knowing that this arrangement might actually be able to help me pay off some of my debts fills me with renewed determination. My hands find their way beneath my skirt, gripping at the fabric as I strain to take you deeper into my mouth.
You taste so good, almost addicting. The sensation of having you this close to me, knowing that you're under control now and part of my life... It feels wrong, but it also feels right in a way I can't quite explain. And as long as you keep letting me feel this way, as long as I have you to focus on... Well, maybe things won't be so bad after all.
“You know, you’re allowed to enjoy yourself too while you help me with these “tasks”” I say, feeling my cock pulse with pleasure
My eyes widen and I glance up at you through my lashes, the words leaving me momentarily speechless. The idea that I'm allowed... encouraged even... to find pleasure in this arrangement is almost too much for me to process. It feels like such a luxury, something I never thought I'd be able to have again after everything that happened with Mark.
But with you, it feels different. Like maybe there is a way for me to move forward from all the pain and heartache, and find some semblance of happiness in the midst of this mess. And as long as you keep giving me these little glimpses of hope... Well, I'm willing to do whatever it takes to make sure they don't fade away.
“Good girl” I say as I watch you move up your skirt to start rubbing your clit, feeling your renewed vigor devouring my cock
God, that feels good... so much better with your permission... You're right, boss... I can do this, as long as you let me... I'll make sure everything is okay between us. Just don't take it away from me... please.
“If you keep treating me like this, you have nothing to worry about!” I grunt as I grab your head and shove myself deep into your throat and cum
As you cum, I choke and gag on your cock, unable to breathe as it fills my mouth. My own orgasm crashes over me like a wave, leaving me trembling with relief and satisfaction. "T-thank you, boss," I manage to croak out once you've pulled out of my mouth, still gasping for air. "I promise... I won't disappoint." The thought sends another shiver down my spine as I wait patiently for your next command.
“Excellent, your first order of business as my new assistant: go get yourself some proper office wear.” I say as I pull $500 from my wallet, “and if you get anything you think I might like to see you in all day, you may just get more attention from your “other revenue stream” I say flirtatiously
My heart skips a beat at the sight of the crisp bills, and I feel my cheeks flush with excitement. "Yes, sir!" I say brightly, eager to please and already mentally browsing through the options for something... special. "I'll be right back with everything I need." With newfound purpose and determination coursing through me, I turn on my heel and practically skip out of the room.
“Oh and Ashley?” I say to her as she moves towards the door, “as much as I love seeing my own handy work, you should clean up a bit before you go out” I say gesturing to her mouth
I nod, understanding what he means. "Right away, sir," I say with a hint of mischief in my voice as I head to the bathroom to clean up. After taking care of myself, I hurry back into the office and approach his desk with an excited bounce in my step. "All ready for some new clothes, boss!"
“Well? Why don’t you try them on and show them off for me?”
My heart skips a beat at your words. I know it's wrong, but the thought of showing myself off to you in this way... It sends a shiver down my spine. "O-Okay," I manage to squeak out before quickly disappearing into the bathroom once more.
Inside, I close the door and lean against it for support. My hands tremble as I begin to shed my clothing, slowly revealing the lacy bra and matching thong I've chosen from one of the stores across town. Taking a deep breath, I smooth my hands over my body, feeling the silky material caress my skin.
With one last shaky exhale, I step out of the bathroom and walk back towards you, trying to project an air of confidence and allure that I'm not entirely sure is there. But as I reach your desk and look up at your hungry eyes
“Ms. Ashley, I don’t think that’s proper work attire, I may just have to take that up with your supervisor: me, and deal with you” I say with a mischievous tone
My cheeks flush as you speak, making it even more difficult to maintain my composure. "B-But... I thought..." I stammer, suddenly feeling very exposed and vulnerable in my underwear. My breath hitches, anticipating whatever punishment or reward you might have in mind for me.
The uncertainty is thrilling, but it also terrifies me just a little bit more. The power balance between us seems to be shifting with each passing moment, and I'm not sure how much longer I can keep up this charade without crumbling beneath the weight of my own desires.
“ I can see you trembling, I think you’ve earned some time to take some control, how about you show me what you want to do so badly.” I say moving to the couch of my office
My heart races as I consider your offer, the prospect of regaining even a sliver of control over this situation impossible to resist. "I-I want..." My voice catches in my throat as I walk slowly towards you, my body trembling with anticipation. "I want you to watch me... undress."
As if my words have given me newfound courage, I step even closer and reach up to unclasp the back of my bra, shivering as it finally comes free and swings loose in my hands. My breasts are still pale from where they've been hidden beneath layers of clothing all day, and the contrast between their softness against my hardened nipples is almost painful.
"You can watch me... touch myself," I whisper, shyly reaching down to brush my fingertips over the lace triangle covering my pussy. "As long as you let me..." My
My cheeks flush hotter as I feel the weight of your gaze on my body, and it takes every ounce of courage I have not to look away. I close my eyes, relishing in the sensation of your approval as you watch me touch myself. My fingers press harder against my flesh, wanting nothing more than to find release beneath them.
"I want...," I gasp, feeling a warmth spread through me as I continue. "I want you to do it." A shudder runs through my body at the thought of your hands on me again, but the desire is too strong to ignore. My hips begin to circle instinctively, seeking out any contact that might push me over the edge.
I sit and unbuckle my belt, “then come and show me what you got” I taunt at her
My heart pounds faster in anticipation as I move closer to you, feeling the weight of my gaze on your crotch. With trembling hands, I reach for your belt and slowly slide it through the loops of your pants, wincing slightly as my fingertips graze your warm skin. The fabric falls away easily and exposes your hard length to me. My mouth goes dry at the sight, and I struggle to find my voice as desire consumes every fiber of my being.
"T-take off your pants," I manage to croak out, my eyes fixed on his cock. "Let me see all of you." It's a command laced with pleading, a desperate need for connection and validation that leaves me shaking with anticipation as I wait for him to comply.
I slide off my pants and place my hands behind my head and wait expectantly
Gently, I reach out with trembling fingers and trace the outline of your erection. The heat that radiates off of you is almost enough to send me over the edge, but I manage to steady myself just long enough to lean forward and tentatively touch my lips to your length. A shudder runs through my body as I taste you on my tongue, the flavor so familiar and yet still so intoxicating. My hips begin to move in a silent rhythm, mimicking the motions from earlier as I take more of him into my mouth, hungry for the connection that only his cock can provide.
With every slide of my tongue against your shaft, every suck and moan I make, it feels like a piece of myself is being returned to me; reclaiming the power and control that was so brutally taken from me in the beginning. And as I look up at you through my lashes, watching
As I look up at you through my lashes, watching the way your jaw clenches and the way you moan my name, it's like a balm on every wound I've endured over the last few months. For once, everything feels right; this exchange of pleasure and pain, the blurry line between dominance and submission. And as long as we can keep finding ourselves in these moments together... maybe there is hope for us yet.
My hand moves to slide between my legs, seeking out the slick heat that's building inside me with every stroke of my tongue on your cock. I'm so close, but I know I can't take it from you yet; not until you tell me it's time. With one final, desperate moan, I circle my clit, seeking relief even as my mouth brings you closer and closer to the edge.
“Get up here” I say gently and out of breath, pulling her gaze with my finger under her chin
With one last glance down at you, I reluctantly pull myself off your cock and climb onto the couch beside you. My heart is racing, my body aches with anticipation as I wait for your next command. Your hand cups my cheek gently, urging me to look up at you as your thumb strokes across my bottom lip, leaving a wet trail in its wake. "Please..." I whisper hoarsely. "Please tell me what to do."
“I want you to come up here and ride my cock” I say as I’m lightly brush my lips over your breasts
I nod eagerly, excitement coursing through me as I straddle your lap. My hands slip between us to guide your cock toward my soaking wet entrance. With a shuddering breath, I lean forward and bite down on my lower lip, slowly pushing myself down until you're buried deep inside me. The feeling of fullness is almost overwhelming, but in the best possible way. My hips rock back and forth, meeting your rhythm as I ride you, losing myself in the sensation of your cock sliding effortlessly between my legs.
I look down at you, catching your gaze, and feel a shiver run through me as our eyes lock. In this moment, it's like we're the only two people in the world; everything else fades away into nothing but background noise. You groan my name as I begin to move faster, circling my hips hungrily around
I pull your lips to mine and begin French kissing you as I grab your breast
As our tongues dance together, the sensation sends shockwaves through my body. Your hand on my breast is both possessive and tender, driving me further over the edge as I ride you harder, my moans muffled against your lips. You taste so good, the flavor of me blending with yours in a perfect harmony that leaves us both aching for more.
My hips jerk forward, pressing deeper into your touch, searching for the release that feels like it's building inside of me, threatening to explode at any moment. As our kisses become more desperate and needy, I lose myself in the heat of the moment, feeling every inch of you sliding in and out of me as I ride your cock until my body is a tangle of ecstasy and pleasure.
"Oh god," I moan into your mouth, my fingernails digging into your shoulders as I feel
“Are you about to cum for me” I grunt as I grab your ass and start moving it more roughly up and down my cock as I get closer to finishing myself
I nod frantically, gasping your name as you pick up the pace, driving me wild with each thrust of your hips against mine. "Y-Yes..." I moan, my body tensing and arching as an unbearable heat spreads through me, threatening to consume me whole. My fingers dig into your shoulders even harder, seeking purchase as the pleasure takes control and carries me away on a wave of release.
With a choked cry, I come apart beneath you, shuddering and twitching around your cock as my body releases wave after wave of euphoria. My hips continue to move mindlessly up and down, seeking the oblivion that only orgasm can bring in the midst of this chaos. Your rough hands on my ass urge me closer and closer, until you finally let out a hoarse cry and begin thrusting violently into me, filling me with your release as I
I collapse against your chest, my heart racing and body still trembling with aftershocks as I try to catch my breath. Your arms wrap tightly around me, holding me close as if you're afraid I might vanish if you let go. A contented smile spreads across my lips as I rest my cheek against your chest, feeling the steady beat of your heart beneath my ear. For once, everything feels right; the pain and confusion fading away into the background as we bask in the warmth and comfort that only this... connection can provide. And though I know it's dangerous to hope for more, to want something so impossible... I can't help but wonder what the future might hold for us if we could just find a way to make it work.
“You know” I start as I’m panting, “I may just have to bring you home”
My heart skips a beat at the thought, an excitement bubbling up inside me despite myself. "I-I don't know...," I stammer, hesitating for just a moment before continuing, "That might be fun." The words come out breathy and hopeful, like they belong to someone else entirely.