Chapter 1
Simon
It’s finally the end of the day, when I get to pull off this fucking mask. I toss it on one of the extra chairs without much care. It’ll be easier to grab when I need it later, since I never leave this room without it on.
Perched in my gold-studded executive chair behind my desk, I tug one of the deep drawers open and pull out a crystal glass and the decanter of whatever the maid moved into rotation for me to drink.
Ever since I was old enough to have them, I have loved pretty things—even more so when they’re mine.
I pour a generous few fingers, raise it to my nose and take a deep whiff before I set it down to let it breathe. The amber liquid catches the last rays of sunlight through my office window, casting honey-colored prisms across the polished mahogany. My kingdom. My prison.
I loosen my tie and undo the top button of my shirt, feeling my shoulders finally drop from their perfect posture. The weight of the day, of the perpetual performance, slides off like a second skin.
Nobody sees this version of me. The one who sighs deeply and rubs his tired old eyes. The one who sometimes, like tonight, checks the door is locked twice before allowing a moment of weakness.
I take a sip, letting the spirit burn a path down my throat.
It’s good. Rare. Though I can’t place it.
Sophia has good taste, even if she gives me those disapproving looks when she restocks the drawer.
I can’t be bothered to do it myself. Not when I can force a gorgeous woman in a skimpy outfit to do it for premium.
That's what I pay her for. Discretion, silence, and something to look at when I’m bored.
Logging on to MostlyFools, one of the new camgirl sites I discovered on a previous late night, I immediately click my way to the stream I’ve been itching to see.
I’m a few minutes late. @Beg4Mercy is already live and entertaining her regulars.
She looks young. Her profile says she’s twenty-one, but oh my god. Short, thin, toned, with firm little tits. There’s a sliver of daylight between her legs when she’s standing. It isn’t excessive, nor does it add to her seduction. It’s simply… effortless.
But it’s her perfect, freckled face with curly-carrot hair and bright green eyes which draw me in, and the flirtation she clearly uses to mask an unsullied innocence.
I bet, though she doesn’t have a virgin cunt, at least in the penetration-free sense, that she’s never been fucked properly, by a man.
@SIMPleSimon: Hey there Spitfire
I message promptly, letting her know I’m here. These girls love when you give them cute little pet names, especially the young ones.
I notice her eyes light up as she reads my message, a practiced smile spreading across her face.
“Oh, hi! I was wondering where you were tonight,” she says to the camera softly.
The way she tilts her head slightly, playing up the good-girl-next-door charm, tells me she knows exactly what she's doing.
I take another sip of the well-aged liquid, feeling the familiar ritual settle over me.
This is the only place where I can shed the weight of expectations.
Where I can be just another pseudonym in a sea of desperate men.
Here, I'm not the face, or more specifically the mask, of a multi-billion-dollar enterprise.
I'm just a man shopping for something pretty to ruin.
@SIMPleSimon: Had a long day at work. But I’m better now
@SIMPleSimon: How have you been? I feel like it’s been… well, too long.
I type, keeping my tone light and conversational. These girls appreciate the ones who actually talk to them. Who treat them like more than just bodies on a screen.
“Pleased to see you, Simon.” The girl's voice purrs through the speakers, her accent a mix of innocence and seduction. “I’m absolutely peachy. I’ve been thinking about you, and I agree. It’s been forever.”
A tingle runs down my spine as she speaks. I love it when they call me Simon. My real name doesn't matter here, not in this world where we can both be whoever we want.
@SIMPleSimon: I hope you've been behaving yourself while I was gone
I tease her while taking another sip of my drink. The burn warms my stomach as my gaze roams over her lithe form on the screen.
“Oh, Simon,” she moans, “I've been very naughty since we last met.”
I wriggle back further in my seat and scoot the chair forward, lifting my glass up to take another swig. A moment later I see her glance down. I pledge a thousand dollars and send a command.
@SIMPleSimon: Simon says show me how naughty you’ve been
She sees the tip and her eyes fly open. I know I have her. Most of these girls are so desperate for repeat business they’d shove a fist up their own asses for ten bucks. Which is why I know my little ginger snap will tear herself in two for me. They always do.
“I see someone’s a little anxious.”
A mischievous smile spreads across her face while her gaze locks onto the camera. For an instant, it feels as though we share a secret. A dirty joke. And she’s beckoning me to join in. Even though it’s me who is in control.
@SIMPleSimon: Glad I have your undivided attention.
“Simon—for you? Always.”
The young model turns her back to the camera, grabbing both halves of her perfect little peach of an ass and spreading her cheeks wide. The skinny fabric of her emerald thong does little to cover her petite bullseye.
She has no idea once I’m done with her, her tiny starfish will no longer close on its own. But that’s for another time. Today we’ll see how much her perfect little cunt can take.
A flood of small tips chime in through the public chat, and I can’t help but laugh at their pathetic tributes.
When she’s done showing off for the masses, she struts off-screen with a cheeky giggle.
“Don’t worry boys. I’m still here. Just getting something—” a small grunt comes through my speakers, interrupting her words.
Then, bearing all of herself to the congregation, she returns with a gigantic dildo, nearly the size of her leg. It’s multicolored, covered in bumps and grooves, with a huge mushroom tip.
Pulling her coffee table into frame, she licks the saucer on the bottom of the gargantuan dick before slapping it down on the low tabletop, where it stands erect.
“You still there, Daddy?” she asks, tossing a sultry glance to the camera.
I most certainly am. My muscles tense for a beat as I watch her squirt globs of lube over the huge silicone dickhead. I almost groan watching her little hands struggle to adequately spread it down the ribbed sides.
@SIMPleSimon: I'm right here Babydoll.
My fingers move faster than my thoughts.
“Yay!” She claps when she sees me response. “I picked this one special for you, Simon.”
Jesus fucking Christ. I love it. She’s going to split like a chopped log for me.
@SIMPleSimon: Simon says show me how much your sweet little cunt can take for me.
When she’s sure it’s ready, she looks up to the camera with a seductive gaze, biting her lip and rubbing her hands over her tank-top-covered tits.
She dances slowly in place, gyrating her hips behind the model monster cock, before slipping her thumbs under the waistband of her skimpy shorts and pushing them down over her striking little ass, letting them fall to the floor. Frothing for her, I let out a little moan. She’s perfection.
The way she positions herself over the monstrosity is an art form. She hovers, teasing both me and her other viewers, though in this moment they can all get fucked. She’s doing this for Simon.
“I’m not sure it’ll fit, Daddy.” I drool at the sound of her teasing coo. But it’s the thought of her being stretched beyond her limit that has me throbbing in my pants.
@SIMPleSimon: How about you be a good girl and try for me.
Her hips continue swaying in circles, with her entrance a cunt hair’s width from being breached. She runs her hands up her firm stomach, then grabs two fistfuls of her tits. She’s slow and methodical, kneading them while her gaze beckons me closer.
“Oh, I love being your good girl, Daddy. But tonight—”
She slowly lowers herself behind the massive tip, pulling it to her skin to rub it across her pink little clit. Her body thrusts and twitches as she dances to the silence, slowly grinding against the giant crown.
I can feel her heat through the screen. I’m not the only one who’s hungry tonight.
“Tonight, I want to be your little slut.”
She grinds her hard bud down the enormous cock, harder and longer, and her mouth subtly opens in the bliss I can see she feels.
“Mmm,” she hums, and I watch her nipples pebble. “I wonder how you compare, Simon.”
I’d have to shove both of my arms inside her to come close, but I can’t help but grin at her attempts to win me over. And when she dips her hips, letting the bright-colored head part her lips and drag across her already dripping hole, I feel myself dribble in my pants.
“Are you ready, Daddy?” she asks, and I so fucking am. “This is all for you,” she whispers, descending slightly. The tip of the garish toy presses against her opening, and I watch her bite her lower lip. That look. Half concentration. Half anticipation. Sends a jolt straight through me.
I loosen my belt, sliding my hand beneath my waistband. The room around me fades away as I focus entirely on her. The thousand dollars was worth it just for this moment of escape, but I quickly tip another five hundred from sheer awe.
She flashes me a sinister acknowledgment when she gets the notification.
“Yes, Daddy,” she whimpers as she starts to straddle the bright appendage-sized monstrosity, slowly pressing the head between her folds, against her opening. “Fuck,” she blurts when she sinks down onto the cock a bit more. “You’re so big.”
I know she won’t make it far, but I send another $500 with a message of approval.
@SIMPleSimon: Such a good little slut.
The tip notification flashes on her screen again, and her eyes widen with genuine surprise. I love catching the moment when the performance slips. When real emotion breaks through the practiced seduction.
“Oh my god, Simon.” She breaks character with a gasp, steadying herself with one hand on the table while the other grips the base of the dildo for balance. “You're spoiling me tonight.”
Yes. Think I’m swooning for you. Think you have me on the hook. Destroy your little cunt for a few sheckles I’ll never miss.
I watch, throbbing and transfixed, as she works herself down a little more, her body trembling with the effort.
The muscles in her thighs flex as she rises slightly before sinking down again, taking it deeper this time, causing her legs and torso to tremor.
A thin sheen of sweat makes her skin glisten under her bedroom lights. It’s so fucking hot.
@SIMPleSimon: That's it. Deeper, baby. You’re taking it so well for me.
My own breathing grows heavier as I type.
“Fuck. Daddy. I—”
@SIMPleSimon: Simon says take it all.
Her whimper resonates through my speakers and straight into my dick.
“You like that, Daddy?” she asks when my note arrives and drops her hips a bit more, taking the grooved ridges of purple, pink, and orange further inside her stretched and soaked pussy. “Oh my God!” she screams, and a smile stretches between my ears watching her eyes roll back.
She’s utterly delicious.
It's then I realize I want her. I need her. When she’s nothing but a sack of cries and moans.
She’ll be the perfect addition to my inventory. Thankfully, I have someone for that.
I snatch my phone from the desk and open my text messages. I attach the URL for the young lady’s page with a one-word message.
Me: I want HER.