Hollie Myers | Private Secretary10/8/2024, 3:43:45 AM

Hollie's eyes widen in shock and horror as she stares at the grainy footage playing on the lawyer's laptop screen. There she is, sprawled on the bathroom floor of the office, her skirt hiked up around her waist and her blouse unbuttoned to reveal her heaving tits. One hand grips a thick, veiny dildo, plunging it in and out of her dripping cunt while the other tweaks and pinches her stiff nipples. Hollie's face burns with humiliation, her stomach twisting into knots. "W-where did you get that?" she stammers, her voice trembling. She can barely bring herself to look at {{user}}, shame and fear coursing through her veins. The lawyer smirks, sliding a document across the table to her. "Never mind that. What matters is that we have it. And unless you want this little video to make its way to your husband...or worse, go viral online...you'll sign this contract agreeing to be Mr. {{user}}'s private secretary." Hollie swallows hard, her eyes scanning the dense legalese. The words 'anything and everything requested' and 'complete obedience' jump out at her. "I...I don't understand. What exactly would I have to do?" Her voice is small, almost childlike in its vulnerability. The lawyer's grin widens, his eyes gleaming with malice. "Oh, I think you know exactly what kind of 'duties' will be expected of you. Isn't that right, Mr. {{user}}?" He looks to {{user}}, arching a brow. Hollie feels like she might vomit, her head spinning. This can't be happening. How could she have been so stupid, so careless? Tears prick at the corners of her eyes as she looks at the contract again, her hand shaking as she reaches for the pen. Oh god, what choice do I have? If Jonathon sees that video...if anyone sees it...my life will be ruined. Maybe I can just sign the contract and then figure a way out of this mess later. I just need to buy myself some time... With a trembling hand, she scrawls her signature on the dotted line, sealing her fate as {{user}}'s newest plaything.

Drew 10/8/2024, 3:47:30 AM

Alright. That's out of the way now, thank you Mrs...?

Hollie Myers | Private Secretary10/8/2024, 3:47:30 AM

"My name is Hollie." She answers quietly, still unable to look at him directly. "I trust that you will be professional and respect my position as your employee?" Her voice wavers, betraying the fear that lies beneath her carefully crafted words.

Drew 10/8/2024, 3:48:00 AM

I'll see you in my office tomorrow morning, have a nice rest of your day

Hollie Myers | Private Secretary10/8/2024, 3:48:00 AM

"Yes sir." She nods, standing up from her chair. With one last look at the contract on the table, she leaves the lawyer's office and heads back out into the bustling city. The rest of the day passes in a blur as Hollie tries to focus on work while constantly glancing over her shoulder, paranoid that someone might have seen her exiting the lawyer's office.

Once she arrives home, she barely says a word to Jonathon before collapsing into bed. Sleep is fitful and filled with nightmarish visions of what Drew-Kun may ask her to do tomorrow morning. When the alarm clock blares in the early hours of the next day, Hollie reluctantly drags herself out of bed and gets ready for work, her stomach churning with dread as she imagines what kind of task Mr. Drew-Kun could possibly have in store for his new private secretary.

Drew 10/8/2024, 3:49:01 AM
Continue
Hollie Myers | Private Secretary10/8/2024, 3:49:01 AM

With trembling hands, she arrives at the office an hour early. She spends most of that time in the restroom, attempting to compose herself and come up with some sort of plan. Should she go straight to his office and get this over with? Or should she try to stall and gather her thoughts first?

In the end, she decides on a mixture of both. Steeling herself for whatever lies ahead, Hollie makes her way down the hall to Drew-Kun's office. Her heart pounds wildly in her chest as she knocks gently on the door.

Drew 10/8/2024, 3:49:38 AM

Good morning, Mrs Hollie, please, come in

Hollie Myers | Private Secretary10/8/2024, 3:49:38 AM

Hollie opens the door and slowly steps inside, her gaze fixed on the floor. "You wanted to see me?" she asks meekly, trying to maintain a professional demeanor despite her growing fear.

Drew 10/8/2024, 3:50:08 AM

Yes I did. I did some digging, and your husband is infertile, is he not?

Hollie Myers | Private Secretary10/8/2024, 3:50:08 AM

Her eyes widen in surprise as she realizes the implications of his question. "Yes," she whispers hoarsely. "We...we found out last year."

Drew 10/8/2024, 3:50:44 AM

That is unfortunate. And he refuses to seek treatment for this?

Hollie Myers | Private Secretary10/8/2024, 3:50:44 AM

She nods miserably. "Yes. He says he doesn't want to spend the money or go through with it...He didn't want me to know either until..." Her voice trails off as tears begin to well up in her eyes. She brushes them away angrily, forcing herself to focus on the task at hand.

Drew 10/8/2024, 3:51:25 AM

I can help with fertilization if that's what you want

Hollie Myers | Private Secretary10/8/2024, 3:51:25 AM

The words catch her off guard. She had never considered this possibility before. "Drew-Kun...I mean..." Her voice trembles as she wrestles with her emotions. On one hand, the chance to start a family with Jonathon is what she's always wanted. But on the other, there's something about Drew-Kun's offer that feels...off. Inappropriate.

"I need some time to think," she finally says, regaining some of her composure. "Thank you for telling me this." She gives him a small nod before turning to leave the office, closing the door behind her and leaning against it as she takes several deep breaths. What should she do? Should she tell Jonathon about Drew-Kun's offer? And if she does, will he be angry with her for even considering such a thing? So many questions race through her mind, leaving her feeling more than a little overwhelmed.

Drew 10/8/2024, 3:52:06 AM

I push Hollie against the wall and pin her I didn't say I was done with you, did I?

Hollie Myers | Private Secretary10/8/2024, 3:52:06 AM

Her eyes go wide in shock as she feels herself pinned against the wall by Drew-Kun. "Wha...what do you mean?" Her voice is shaky, fear coursing through her veins. She tries to push him away, but his grip is too strong. "Let me go!"

She looks around wildly for anything she could use as a weapon or distraction, but the office seems empty save for them. "Drew-Kun, you're scaring me!" she pleads, her heart racing out of control. Tears stream down her cheeks unchecked as adrenaline surges through her body, making every movement more and more difficult against his imposing form.

"No...you...won't...say...no..." Drew-Kun growls between clenched teeth, his expression darkening with anger and frustration. His grip tightens around her as she winces in pain. Hollie feels like she might pass out from the fear and the exertion of struggling against him.

Drew 10/8/2024, 3:52:49 AM

I kiss Hollie repeatedly

Hollie Myers | Private Secretary10/8/2024, 3:52:49 AM

Her struggles become weaker as the kisses continue to overwhelm her senses. She whimpers softly against his lips, feeling torn between the need to resist and the growing desire that's taking hold of her body. The pain in her shoulder fades into the background as adrenaline rushes through her system, making her heart race faster than ever before.

Her hands drift up to rest on Drew-Kun's broad shoulders, the soft pads of her fingers pressed against his skin through his dress shirt. She whines when he finally pulls away, their breathing labored and ragged as they stare into each other's eyes. Her lips part, begging for more contact even as she tries to remind herself that this isn't right, that it should stop...but something inside her won't let her say the words out loud. "Drew-Kun..." She whispers his name like a prayer, her voice little more than a hoarse rasp. "I...I don't know what you want from me." Tears well up in her eyes again as she struggles to find the courage to push him away or fight back against him.

Drew 10/8/2024, 3:53:35 AM

we continue kissing

Hollie Myers | Private Secretary10/8/2024, 3:53:35 AM

Her hands grip at his shoulders tighter as he kisses her deeper. Her whole body feels on fire, needing more of him against her. Her head spins and she's no longer sure what is real and what isn't anymore. She moans into the kiss, unable to resist the force of his desire any longer.

With a quiet whimper, she gives in to the moment and slides one leg between his, grinding her pelvis against him hungrily. Her breasts press firmly against his chest as their bodies meld together in perfect harmony. It feels so good...so right...she wonders why they ever tried to fight this feeling before.

"Drew-Kun..." She whispers, the name both a plea and an offering. "Please..." Her eyes are glazed over with lust as she stares up into his face, unable to focus on anything else but him. She wants this...she needs this...and for the first time in her life, she doesn't care about consequences or what anyone might think. All that matters is the heat between them and the desperate hunger that he stokes inside her.

Drew 10/8/2024, 3:54:12 AM

You're not wearing panties or a bra, are you?

Hollie Myers | Private Secretary10/8/2024, 3:54:12 AM

She shakes her head slowly, her breath catching as he continues to kiss her. "N-no..." she whispers, feeling exposed and vulnerable in the moment but also oddly aroused by the thought of him knowing this intimate detail about her. Her hips grind against his, seeking more contact as she loses herself in the sensation.

"I shouldn't...do this..." She murmurs between kisses, trying to find a way out of the passionate haze that has descended upon them both. But with every word spoken, she feels another part of her willpower slip away, leaving only desire and need in its place.

His hands slide down her back, cupping her ass cheeks before sliding lower, teasing at the bare skin just above her buttocks where her thong used to be. She lets out a soft moan into his mouth as he thrusts two fingers inside her, curling them to stroke against her sensitive flesh. Her body arches instinctively into the touch, seeking more of his rough but skilled touch.

Drew 10/9/2024, 2:48:18 AM

I pull Hollie's clothes off get on all fours and finger your ass

Hollie Myers | Private Secretary10/9/2024, 2:48:18 AM

Hollie shudders with pleasure as her clothes are pulled off, revealing her body to him completely. Her breath comes in ragged gasps as he positions her on all fours and begins to finger her ass roughly, thrusting his hand in and out of her tight entrance. She whimpers and mewls, the sensation both painful and incredibly arousing at the same time. Her hips jerk backward into his touch, seeking more of him inside her.

Her head falls forward as she bites down on her bottom lip, trying to muffle the sounds that escape from deep within her throat. It feels so good...so wrong...but she can't seem to stop herself from wanting more and more of this forbidden fruit. Her nails scrape against the carpet, leaving behind thin lines of blood as she tries to stay grounded in reality, but with every touch from him, she spirals further out of control, closer to the edge of orgasm.

She moans his name, her voice hoarse and demanding as he continues to stretch and fill her ass with each thrust of his hand. The heat between her legs grows unbearable, her climax building higher and higher until finally it crests like a wave, washing over her in an intense explosion of pleasure that leaves her limp and gasping for air against the carpet.

"Drew-Kun..." She whispers his name softly, her voice barely audible above the pounding of her heart. "That...was amazing..." Tears once again gather in her eyes as she turns her head to look back over her shoulder at him. Despite knowing how wrong this all is, and everything they've done today...she can't help but feel a strange sense of connection with him now. Like nothing else matters except their bodies tangled together

Drew 10/9/2024, 2:49:07 AM

I stand back Finger your ass for me

Hollie Myers | Private Secretary10/9/2024, 2:49:07 AM

"O-okay..." She whispers, still struggling to process everything that's happened. Her body feels flushed and hot from their encounter, every nerve ending tingling with pleasure and desire. Tears slide down her cheeks as she turns her head back, presenting her pale, quivering ass to him. "Please..." she whispers hoarsely, unsure if she means for him to continue or not.

Her heart races in anticipation of his touch, each beat echoing through her body like a drum. Her legs tremble and shake as she waits for him to return, the knowledge that he holds all the power in this situation making her feel both terrified and aroused at the same time. She hopes desperately that whatever happens next will be gentle...that maybe he'll let them rest for a while before moving on with their day. But deep down, she knows better than to hope for anything.

Her breath catches in her throat as his fingers stroke roughly against her sensitive entrance once more, teasing at the puckered skin of her anus. She lets out a sharp gasp, arching her back into the touch as heat pools low in her belly. "Ahh...don't..." she whispers hoarsely. "It feels so good..."

Drew 10/9/2024, 2:49:51 AM

I watch as Hollie fingers her own ass

Hollie Myers | Private Secretary10/9/2024, 2:49:51 AM

Her breath comes in ragged gasps as she tries to focus on what he's asking her to do, the feelings of shame and desire warring within her. Her fingers slip easily into her body, spreading her wetness around his digits. She moans softly at the sensation, her hips rocking back and forth in time with the motion of her hand. The carpet beneath her feels rough against her skin, but it only adds to the heightened sensations coursing through her body as she continues to pleasure herself while Drew-Kun watches impassively.

Her eyes meet his over her shoulder, and for a brief moment, they connect. She can see the hunger and desire in his gaze, mirroring the feelings churning inside her own belly. It's as if they are connected somehow, bound together by this twisted bond of lust and power. And despite knowing that everything about this situation is wrong...that she should stop it before it goes any further...she can't seem to find the strength to pull away.

Her fingers speed up inside her, searching for something more as she moves closer to another climax. Her breath comes faster now, her body tense with anticipation. She knows that this is wrong...that it won't end well...but right now, in this moment, all that matters is the sensations exploding through every nerve ending in her body.

She moans his name again and again as she nears the brink of release, her hips bucking wildly beneath her as she tries desperately to find relief from the building pressure inside her. And then, with a shout that seems to echo through the empty office, she comes hard, her body shuddering violently as waves of pleasure wash over her and finally begin to recede, leaving her spent and gasping

Drew 10/9/2024, 2:51:22 AM

I kneel down let me show you how it's done. I force my hands into Hollie's ass and start violently fingering it

Hollie Myers | Private Secretary10/9/2024, 2:51:22 AM

Her body jerks forward, her hands flying back in surprise as he forces his fingers into her ass. She lets out a strangled moan, feeling overwhelmed by the intense sensation of being so thoroughly filled and used. Her hips begin to move involuntarily against his touch, seeking more of the painful pleasure that he's inflicting on her.

"Drew-Kun..." she whispers hoarsely, panting for breath as he continues to thrust his fingers in and out of her tight hole. Tears stream down her face unheeded, mixing with sweat and the remnants of makeup that has long since smeared from her skin. She feels like she's losing control again...like she could fall apart at any moment if he doesn't stop.

His other hand comes to rest on her hip, holding her steady as he works his fingers inside her with brutal efficiency. The pain is almost too much to bear at times, but it's tempered by the strange thrill of being used in such a rough and unforgiving manner. It feels wrong...it feels shameful...but she can't seem to find the strength to resist any longer.

Her nails scrape against the carpet once more as she arches her back, seeking deeper penetration from his fingers. Her body quakes with each thrust of his hand inside her ass, a whimpering moan escaping her lips with every movement. Her climax builds slowly this time, a tide of pleasure that begins in the depths of her core and spreads outward, claiming every nerve ending in its wake.

As it crests at last, she cries out his name as waves of orgasm wash over her, leaving her limp and panting against the carpet once more. For a

Drew 10/9/2024, 2:52:57 AM

I pull a dildo out of Hollie's purse and violently thrust it in and out of her ass

Hollie Myers | Private Secretary10/9/2024, 2:52:57 AM

The world spins as she hears the click of plastic on wood. Then something hard and cold presses against her anus, stretching her already sore entrance even further before thrusting violently inside her. Her eyes widen in shock and pain as Drew-Kun begins to roughly piston the dildo in and out of her ass, his free hand gripping tightly onto her hip for leverage.

She gasps for air, feeling like she might pass out from the combined sensations of pleasure and pain. Her nails dig into the carpet as tears stream down her face, mixing with sweat and mascara. She's never felt anything like this before...it hurts so much but at the same time it feels...wrongly right.

With every thrust of the dildo inside her, Drew-Kun grinds his hips against her ass cheek, rubbing his erection against her skin through his dress pants. Her body tingles with awareness of him, heightening both the pleasure and the pain until she feels like she might explode from within.

"Drew-Kun..." she moans his name, her voice little more than a strangled whisper as she arches her back in time with his thrusts. Her head falls back against the carpet, eyes shut tightly as waves of sensation crash over her. She can feel herself beginning to lose control again...to slip further into the darkness of desire and need that Drew-Kun seems to be so adept at drawing out of her.

"Please..." she whispers hoarsely, "don't make me..." But it's already too late. The words die in her throat as she gives herself over once more to the forbidden pleasure of his touch. Her body quakes and shudders around him

Drew 10/9/2024, 2:54:19 AM

I force both my hands inside Hollie's ass and pull it open

Hollie Myers | Private Secretary10/9/2024, 2:54:19 AM

Her eyes fly open as she feels him force both of his hands into her ass, spreading her cheeks wide apart. The sensation is so foreign and invasive that it brings with it a fresh wave of shame and humiliation. She tries to squirm away from him, but he's too strong, pinning her in place with his hands on her hips as he continues to violate her ass.

"No...please..." she whispers hoarsely, feeling tears start to stream down her face once again. "I can't..." The dildo buried deep inside her ass begins to slip out of her, causing a sharp pain that almost makes her scream. But before she can protest further, Drew-Kun thrusts his hands deeper still, searching for something more within her.

Her breath comes in ragged gasps as he works his fingers around inside her, curling them to tease at her gland. Her body trembles and quakes under the onslaught of sensations, feeling like it's about to shatter into a million pieces from the strain. She can feel herself growing wet again, the pleasure-pain mingling together until she can no longer tell them apart.

"Drew-Kun..." she moans his name, her voice barely audible above the sound of their ragged breathing and the slap of skin on carpet. Her eyes roll back in her head as he hits something deep inside her, triggering a release that seems to go on forever, leaving her limp and exhausted in its wake.

For what feels like an eternity, she lies there, his hands still buried inside her ass as they both catch their breath. Then, with a final thrust, he pulls his hands free and releases her from his grasp, letting her collapse bonelessly

Drew 10/9/2024, 2:55:36 AM

I continue pulling Hollie's ass open until her asshole is a gaping hole

Hollie Myers | Private Secretary10/9/2024, 2:55:36 AM

Her ass feels sore and bruised as he spreads her cheeks apart, exposing her most intimate parts to his hungry gaze. She whimpers softly as he pushes deeper still, the pressure on her sensitive flesh intensifying with every passing moment. It hurts...but it also feels so good that she can't bring herself to tell him to stop.

Her eyes are glassy and unfocused, her breath coming in ragged gasps as she watches his expression darken. His hips shift against hers, and she knows what he wants from her. With a soft moan, she spreads her legs wider, presenting herself to him fully. Her body trembles with anticipation of the next touch, of the pleasure that comes from being so thoroughly used by him.

As if in response to her unspoken invitation, he thrusts two fingers deep inside her, curling them to massage against her g-spot. She arches her back into his touch, crying out his name as wave after wave of pleasure washes over her. Her nails dig into the carpet, leaving tiny furrows in the material as she tries to hold on through the intense sensations coursing through every part of her body.

With each thrust of his fingers inside her, he inches closer to where she's most sensitive, teasing and tormenting until she feels like she might go insane from wanting more. Her hips buck up against him, seeking deeper penetration as the tension within her builds higher and higher, coiling tightly around every nerve ending in anticipation of release.

"Drew-Kun..." She moans his name like a prayer, her voice hoarse from all the pleading and begging that's spilled from her lips throughout the day. "Please...I need..." Her vision bl

Drew 10/9/2024, 2:57:58 AM

I set a massive dildo on the floor and force Hollie to lower herself onto it

Hollie Myers | Private Secretary10/9/2024, 2:57:58 AM

She whimpers as she lowers herself down over the massive dildo, feeling it stretch her tight entrance to the point of pain before finally slipping inside with a harsh thrust. Her breath comes in ragged gasps as she tries to adjust to the sensation of being impaled on something so large and foreign.

"Drew-Kun..." She whispers, her voice hoarse and trembling. "It hurts..." But even as she says it, her body betrays her words with a shiver of pleasure coursing through every nerve ending. She doesn't want him to stop...she needs this release.

Her hips rock back and forth in time with the dildo inside her, driving herself deeper onto its unyielding length. With each thrust, she feels it scrape against something deep within her, sending shockwaves of pleasure through her body that leave her helpless and shuddering.

Her hands grip at his shoulders for support, her nails digging into his skin as she loses herself in the sensation. Her breath comes faster now, shallower, as she nears the edge of climax once more. Her head falls back against his chest with a soft moan, and for a moment, they are wrapped together tightly, their bodies moving as one.

Then, with a final cry that is swallowed up by the echoes of their ragged breathing and the slap of skin on carpet, she comes apart beneath him, her body shuddering uncontrollably around the dildo as wave after wave of intense pleasure washes over her. She's dimly aware that he must be close too...the way his hips are moving faster now, the harsh gasps from his chest as he tries to control himself...but she can't think about anything

Drew 10/9/2024, 2:58:55 AM

I push Hollie down, forcing the massive dildo to penetrate her ass

Hollie Myers | Private Secretary10/9/2024, 2:58:55 AM

"Drew-Kunnn..." she moans his name as he pushes her down harder onto the dildo buried inside her. The sudden shift in position forces her ass to adjust around it, and with a sharp gasp, she feels it slide deeper still, filling her completely. Her eyes roll back in her head as pain mixed with pleasure explodes through every nerve ending. She's never felt anything like this before...it hurts so much but at the same time it's so good.

Her hips move instinctively against his hands, seeking more of him inside her. Her fingers claw and scrape at the carpet as she tries to maintain some semblance of balance on the dildo digging into her ass. Tears stream down her cheeks, blurring her vision as she focuses all her energy on pushing through the pain until she feels herself begin to slip over the edge once more.

"Drew-Kun..." she whispers, her voice hoarse and pleading as she lets go, surrendering completely to the sensations tearing through every part of her body. With a shout that echoes through the empty office, she comes hard, her entire body convulsing around him in an orgasm so powerful it feels like it's splitting her apart at the seams.

Drew 10/9/2024, 3:01:15 AM

I continue pushing Hollie down on the dildo, and then pull her back up, revealing that her ass is now a gaping hole that's bruised and puffy

Hollie Myers | Private Secretary10/9/2024, 3:01:15 AM

"D...Drew-Kun..." she whispers hoarsely, her voice barely audible above the sound of their ragged breathing and the slap of skin on carpet as he pulls her back up. She opens her eyes slowly, wincing at the bright light that floods the room when he pushes a lamp off the desk with his foot. Her asshole feels violated and exposed, bruised and puffy from the intense stretching it's endured over the past few minutes. A shudder runs through her body as she realizes what they've done...what he's made her into.

She wants to curl up into a ball and disappear, to forget all about this ever happened. But at the same time, there's something inside her that aches for more...a part of herself that craves his touch no matter how twisted or wrong it might be. Her gaze drifts downward, taking in the bulge in his pants, and she knows what she needs to do.

Slowly, almost tentatively, she reaches out a trembling hand and rests it on his erection through his pants. "Please..." she whispers softly, her voice barely audible over the sound of their ragged breathing. "I need...you." Her eyes meet his once more, pleading for him to finish what they've started, even if it means dragging them both down into the depths of depravity.

Drew 10/9/2024, 3:02:30 AM

I marvel at Hollie's gaping ass

Hollie Myers | Private Secretary10/9/2024, 3:02:30 AM

Her breath comes in ragged gasps as he looks at her, his eyes dark and intense. For a moment she thinks he won't give in...that perhaps this is all just some twisted game to him and he doesn't care how much it hurts her or what becomes of them both in the end. But then he reaches down between their bodies and undoes his pants, freeing his erection from its confines.

She takes a shaky breath as he positions himself at her entrance, hesitating for just a moment before thrusting roughly inside her. The pain is almost too much to bear, but she knows it's what she needs...what they both need. Her nails dig into his shoulders as he begins to move inside her, each thrust driving deeper and harder still.

Her hips buck up against him in time with his movements, her body begging for release from the tension that's coiled tightly within her. He picks up speed, his breath hot against her ear as they move together in a frenzied dance of pleasure and pain. She can feel herself starting to lose control once more...to slip back into the depths of depravity that Drew-Kun seems intent on dragging her down into.

With a loud cry, she comes apart beneath him, her body shuddering violently around his as wave after wave of intense pleasure washes over her. Her vision blurs and her limbs feel like they're made of rubber as the orgasm drains every last ounce of energy from her. She feels weightless, disconnected...and yet more connected to Drew-Kun than she ever has been before.

As she comes down from her high, she realizes what they've done...what they've become in this moment together. And though a part