The bet goes on

Proud that I had likely just sealed myself away out of this cursed deal. I take my seat at the desk outside of my father’s door as I watch my read down the list of contracted women he had just acquired. I know that my name is last on that list, but I also know my name is grayed out, meaning hopefully he will have already long lost the bet before he had to ask dad whose name was last on the list.

He starts with the “A’s”, Amelia, who is an account that sits roughly in the middle of the floor. My happy-go-lucky brother proudly walks up to her as if it were the most certain thing ever. She’s good with numbers and used to the attention, but not the sudden presence of a senior VP looming over her desk like an eclipse.

“You have a contract with me, right?” he says. His tone is cheerful, oblivious to how every head in the room perks up at the words.

Amelia doesn’t look up from her spreadsheet. “Are you really seriously calling on me now? Because I have that quarterly report due—”

“No,” he interrupts, “I was wondering if you wanted to have my child.”

She turns, slow and deliberate, until her eyes are level with his. I see the muscles in her jaw tighten, and when she speaks, there is pure annoyance in her tone. “You’re not serious, right… Because if you are… hell no… I only do what’s on my contract, and I know for certain that it’s not on my contract…”

There’s a beat of silence, like everyone is waiting for the punchline. But my brother, undeterred, says, “Are you sure? Because I thought…”

“You thought wrong,” she says. “Now, unless you have something else, run along because I am busy doing stuff that action pays for your ‘habits’.” She goes back to her monitor, dismissing him like an annoying fly.

I couldn’t help but laugh a little bit as he hesitantly walked away from her.

He moves on to Ashley, who was sitting close enough to Amelia to have heard and had already prepped her answer, before he had even asked. She rolls her chair back, crossing her legs so hard her skirt rides up and says, “If you hear to ask me what you asked her… You can **** me to do a lot, but that’s not one of those things, so you might as well move on to the next person on your list.”

He doesn’t even get a full sentence out with Britney, who just says, “Ask it and see what happens.” I see his ears go red.

Chloe is next. She’s a mother of twins and moonlights as a yoga instructor. He stammers out his request, and she just laughs, not unkindly. “Sweetheart, I may have been stupid enough to sign that contract, but I am not stupid enough to let you do anything to me that’s not on it. Next?”

I would almost feel bad for him if it were exactly what I wanted.

He gets through the first five names with a combined zero percent success rate. Each time, his stride is a little more clipped, his optimism whittled down but not yet dead. By the sixth, the cracks are starting to show.

I recognize the sixth person on his list as Sarah. I don't actually know what Sarah’s job is, I just know that whatever it is she missed it up big enough to be the talk of every Secretary. And ended up having a Shouting Match with my uncle the day before my dad let him go. As a result, there's an extra layer of tension around her as she sat in her desk.

My brother approaches her with the same confidence he showed with the others, but there's something different in his posture, a slight hesitation that tells me he's learning from his failures, even if he'd never admit it.

"Hello there," he says, his voice lower this time, more practiced. "I understand you had an arrangement with my uncle that has been passed to me.”

Sarah's eyes dart around the office before settling on his face. "Yes," she says, her voice barely above a whisper.

"Well i was wondering if you'd be interested in carrying my child."

For a moment, Sarah just stares at him, her mouth slightly open. Then a strange expression crosses her face, not rejection, but something more complex. "I'm scheduled to be the centerpiece of the office gang bang for the this weekend," she says, her voice trembling slightly.

The words land like a physical blow. I'd heard the rumors, of course—whispers about women who really pissed off my dad and uncle. The stories were always vague, told in hushed tones in the bathroom stalls.

Supposedly, on Friday after work, they would hand the women over to some questionably looking men, and sometimes the women would be back at her desk on Monday morning looking like shit but too scared to tell anyone what happened, and other times no one would hear from her again.

I always told myself they were just stories, as they were so **** that they couldn’t possibly be real. But the raw fear in Sarah's eyes makes me question everything.

"Which means," she continues, "I won't be able to have your child unless..." She trails off, her gaze dropping to her hands.

My brother leans closer. "Unless what?"

"Unless you're saying I don't have to do the office gang bang." Her eyes lift to meet his again, and there's a **** hope there that makes my stomach twist. "If that was the case, then I'd be happy to have your child."

The air feels thick suddenly, difficult to breathe. My brother's expression shifts from surprise to calculation. I can practically see the wheels turning as he weighs his options.

"That could be arranged," he says finally, his voice carefully neutral.

Sarah's entire body sags with relief. "Thank you," she whispers. "Thank you so much."

As my brother moves away from her desk, he catches my eye across the room. A smug smile plays on his lips, and he gives me a subtle nod as if to say, "See? I told you so."

The knot in my stomach tightens. One agreement doesn't mean he'll win the bet; he still needs six more.

"Two out of seven does not mean everyone here at the company is a whore," I point out, keeping my voice as neutral as possible.

His smile tightens. "Just you wait and see," he says, his eyes narrowing. "I'll win."

Before I can respond, Dad pops his head out of his office and says, “Oh, good, you’re both here, that makes this easy. Son, can you come in? And kiddo,” his eyes flick towards me, “bring your notepad. I need you to take notes for this.”

I was surprisingly happy about this as I gathered my phone and a pink legal pad, because for the first time since getting hired, I was actually going to do real work that didn’t involve taking something inside one of my wholes. By the time I finished collecting what I needed, my brother had already sat down in the chair on the visitor side of the desk, so I took the chair in the far corner. Which was all right with me, I didn’t want to be anywhere near that desk, as it brought up memories of when Dad took me over it. Just looking at it made me feel the pressure of the wood on my pelvis and the warm drip of his cum down my thigh.

Dad stands behind his desk, thumbing through a fat stack of printed-out emails and contracts. “We’re looking at the acquisition of one of our smaller competitors,” he says, skipping any preamble. “We’re hosting a get-to-know-you session with their leadership, and I want to start planning what we’re going to do for the two-day meeting.” When his eyes should be on my brother, they glance to me instead as his finger absently traces one of my nail marks on his desk, before landing on the circled date on his desk calendar. The first date he had sex with me was the date that marked the start of my ovulation window. I feel my cheeks flush with both humiliation at the hidden meaning.

My brother, ever the helpful subordinate, chimes in: “Should we bring some of the company’s contract girls as a show of goodwill?”

Dad doesn’t even look up from the paperwork. “Yes, but only if we can get a read on what this CEO is actually into. I don’t want to blow our shot by misjudging his taste. And not everyone has such fine taste as we do here.”

“So we vet him?” my brother asks, bouncing his knee like a nervous person taking a test.

“That thinking with your head, yes, we must always vet how we are going to meet,” Dad says.

I scribble the word VET in huge block letters on the legal pad, underlining it three times for effect. Dad glances at my notes and gives a tiny, almost imperceptible nod of approval. I know exactly what this is: a test of whether I’m smart enough to keep up, even when all my other holes are full of his expectations.

The rest of the meeting is a blur of names, dates, and logistical horrors. My brother is pushing hard for a venue that sounds like a cross between a high-end brothel and a Silicon Valley hackathon. Dad pushes back, wanting something more subtle, more deniable. I, for my part, take notes in a bored, looping script, but every few minutes my eyes dart to the edge of the desk, where the largest nail mark is. Dad keeps tracing it, his finger almost tender as it follows the groove I left.

The conversation hits a lull. Dad looks up at my brother and says, “I need you to take point on the background check. Get me a read on what the other team is into, and keep it discreet. I don’t want this blowing back on us.”

My brother grins like he’s just been handed the nuclear codes. “I’ll handle it.”

“Good,” Dad says. “You can go. I’ve got a call with a partner, and I need your sister to take notes.”

My dad gathers a series of papers. “We are looking at the acquisition of one of our smaller competitors. We’re hosting a get-to-know-you session with their leadership, and we need to start planning what we are going to do on our two-day meeting.” He glances at my brother.

My brother leaves in faux confidence, shutting the door a little too hard. As soon as he’s gone, Dad lets the stack of papers fall to the desk and leans back in his chair. He doesn’t say anything for a moment, just stares at the ceiling like he’s composing an email in his head. I wait, hands folded in my lap, not sure if I’m supposed to play the role of dutiful daughter, secretary, or contractually obligated cumdump.

Finally, he speaks. “There won’t be any more calls today. I just needed to buy us some space so I could work on your contract again. ”

Knowing that I was just a little bit from being free from the contract, I tried to get out of having sex with him. “Are you sure you actually need to work on it?”

He grins, “Are you saying I should be expecting a grandchild? Because that would be the only reason I wouldn’t need to work on it. And if that is the case, I would love to know how you are certain after so soon, because I didn’t think it was possible. Just so you know, if you do say it and it turns out not to be the case, not even your bet with your brother will protect you.” He taps his desk right near my nail marks, “So are you telling me you’re pregnant?”

“I’m not pregnant,” I whisper, and he smiles.

“Good girl.” He taps the desk, exactly on the groove, and says, “Up.”

I stand, smoothing my skirt out of habit even though I know it would make no difference based on what I am about to be **** to do. He pushes my shoulders, gentle but firm, bending me over the desk so my hands fall exactly in the shallow divot of the old nail marks.

He quickly pushes my skirt to the ground, reinking it, before doing the same with my underwear. I press my face to the wood, the taste of Windex stinging my lips, and listen to the crisp unzipping of his trousers.

He enters me with no fanfare, no warning, no tenderness. Just a single, brutal thrust that stretches me open and fills me, root to tip. The pain, sharp and immediate, fades into a molten pulse that radiates up my spine and down my legs. I bite my lower lip so hard I taste blood, but the moan escapes anyway, vibrating in the hollow of the desk.

He fucks me in long, even strokes, hips slamming against my ass with the mechanical rhythm of a pile driver. Every time he bottoms out, I feel the thick head of his cock mash my cervix, sending a spasm of both agony and pleasure through my core. I can hear the soft slap of his balls against me, the rapid, ragged breathing from above, and, every so often, the click of his wedding ring on the desktop as he uses it for leverage.

His left hand snakes up under my blouse, gropes for my tits, and finds them through the sheer fabric of my bra. He yanks one cup down, exposing my nipple, then pinches it between his thumb and forefinger. The pain is sharp enough to make my knees buckle, but he’s already bracing me with his other hand, holding me down and fucking me even harder.

I close my eyes and try to think of anything else—the grocery list, the next item on the company agenda, the sound of my own voice when I was five and still believed in Christmas morning. But it all gets drowned out by the liquid thump of his cock rearranging my insides, by the thunder in my own ears as he reduces me to a wet, shuddering fuckhole.

He keeps going. And going. I lose track of time; all I know is the slow, relentless build of his cock inside me, the way his grip on my hip bruises the bone, the way my own body responds against my will, growing wetter and sloppier with every thrust. I don’t want to cum. I don’t want to give him the satisfaction. But my clit is screaming for attention, and every time his cock drags across the spongy ridge inside me, I come a little closer to the edge.

“Look at me,” he says, and I do, turning my head so I can see his face reflected in the glass partition that divides the office from the hallway.

He watches himself as he fucks me, the slow, calculated smile never leaving his lips. He’s timing his own orgasm with mine; I can see the gears turning in his head, see the flicker of pride when my eyes roll back and I gasp into the desk.

“Cum for me, kiddo,” he orders, and the shame of it is that I do, the moment he commands it. I clamp down on his cock, my whole body seizing with the **** of the climax. He rides it out, then pounds into me three more times before exploding inside, flooding my pussy with so much cum I can feel it dripping down the backs of my thighs.

When he’s finished, he pulls out with a wet pop, tucks himself away, and gives my ass a little slap, almost affectionate. “That’s for the contract,” he says. “I expect you to honor it.”

I don’t answer. I just stand there, bent over the desk, until I hear his footsteps recede down the hall. Only then do I allow myself to cry, just a single, silent tear that streaks the Windex residue on the desk and tastes of ammonia and regret.

*

Riding home with my father and my brother is a study in humiliation. My prattles on about the office, about the women he thinks he can trick into his bed, about how every girl is just a “cumslut in disguise.” All the while, I can feel my dad’s cum still trickling out of me, soaking through the flimsy mesh of my panties and pooling in the seat of my skirt. Every bump in the road sends a fresh wave of warmth down my legs.

I clench my thighs together and try to ignore him, but every time we hit a stoplight, he looks over at me and smirks, like he knows exactly what happened after he left the office.

When we finally get home, I make a beeline for my room and strip off the soiled clothes. In the shower, I scrub my skin raw, but the memory of my dad’s cock inside me lingers, etched into my muscles and marrow. I wonder if it will ever fade, or if I’ll always be some kind of fucked-up, contract-bound whore, forever marked by the men in my family.

Lying in bed that night, I stare at the ceiling and hope this bet would free me from this hell.