Cover of From Zero to Casanova

From Zero to Casanova

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This is a story about a 30 year old nerdy black man who goes from frustrated sexual virgin to a man with a roster full of women who calls him “Daddy.”

Chapter 6: Brooke the MILF

The encrypted drive sat on his kitchen counter like a stray bullet. Jerome stared at it while coffee brewed, its bitter smell cutting through the lingering scent of Bianca on his skin. Thursday was a tectonic plate grinding toward him. He had the ledger data, the film, the agreement. He had a role to play. And yet, the core instruction from his first night with Coco echoed: Learn.

He needed to understand the ecosystem, not just from the top with Serena, or from the shadows with Bianca, but from the ground. From the women who were both the currency and the engine. He needed to see the machine from the inside of a different gear.

His phone buzzed. A number he didn’t recognize. The text was straightforward:

Coco says you’re a quick study. Bill’s. 3 PM. Ask for Brooke. He deleted it, but the address was already a pulse behind his eyes.

Dolla Bill’s at three in the afternoon was a different beast. The neon was off, the stage dark and empty. The air smelled of industrial cleaner and stale beer, the glamour scrubbed away to reveal the dingy bones of the place. A single work light illuminated the bar where Bill sat, counting a stack of bills with the focus of a surgeon.

“Jerome. Punctual.” Bill didn’t look up. “Brooke’s in the back. VIP 3. She’s expecting you.”

“What’s the lesson?”

Bill finally glanced at him, a flicker of appraisal in his flat eyes.

“The lesson is, everyone’s sellin’ somethin’, kid. Even the ones who seem like they’re just buyin’. Brooke’s a real estate agent. She sells dreams of picket fences and granite countertops to couples by day. By night…” He shrugged, a massive movement of his shoulders. “She sells a different dream. A simpler one. She’s been in the game longer than most of these girls have been alive. She knows the score. Listen to her.”

VIP 3 was a curtained alcove, plush in a worn, sticky way. A woman sat on the circular velvet booth, her back to him, looking at her phone. She was older, maybe mid-forties, with a cascade of honey-blonde hair that looked expensive. She wore a sharp, cream-colored pantsuit that screamed professional success. When she turned, her face was handsome, clever, with laugh lines around her eyes and a mouth that suggested it knew how to talk its way into or out of anything.

“You must be the prodigy,” she said, her voice a warm, cigarette-tinged alto. She didn’t smile, just looked him up and down with a frank, unimpressed assessment. “Coco says you’re a sponge. Bill says you’re walking into a hornet’s nest. Sit down. You want a drink? They’ve got bottled water back here. Or shitty whiskey.”

“Water’s fine,” Jerome said, sliding into the booth opposite her. The velvet was cold.

She produced two cold bottles from a small ice bucket beside her, twisted the cap off one, and handed it to him.

“Brooke Ashford. I hear you’re getting a crash course in applied femininity.”

“Something like that.”

“Coco taught you how to fuck. Bianca’s teaching you how to fight. Serena’s teaching you how to scheme.” She took a long pull of water. “I’m here to teach you about the actual product. Not the girls. The dream. The fantasy. It’s the only thing that’s real in a place like this.”

She leaned back, crossing her legs.

“Once upon a time, I was a Hooters girl in the 90s. Spring Break wet t-shirt champion in Panama City, 1998. Three years later, I won a twerk contest in South Padre. Posed nude for websites when that was still a novelty. Now I have an OnlyFans that pays my mortgage and a real estate license that gets me invited to garden parties. I’ve been the fantasy for bankers, for lawyers, for sad suburban dads, for tech bros like you. I know what they want before they do.”

“And what DO they want?” Jerome asked.

“Depends on the man. The hungry ones want validation. The powerful ones want degradation. The lonely ones want girlfriend experience—they want to pay for the memory of someone giving a shit. The cruel ones want to see how much they can take.” Her gaze was unnervingly direct. “But at the core? They want to feel like they’re the only one. Like this moment, this transaction, is a secret rebellion against their boring, controlled lives. Your job, if you’re gonna be more than a mark, is to make them believe that. Even when you’re thinking about your damn grocery list.”

Jerome thought of Diamond’s empty smile on Eckles’ lap.

“Sounds exhausting.”

“It’s a performance. Like selling a house with a foundation problem. You highlight the vaulted ceilings, you bake cookies, you don’t mention the termites.” She finished her water. “Coco said you needed to understand the perspective. So. You’re not here to fuck me. You’re here to watch me work. Consider it a masterclass.”

She stood up, smoothing her pantsuit.

“My next appointment is in ten minutes. A regular. Divorced, mid-fifties, venture capitalist. He likes to feel young. He likes to feel like he’s corrupting something sweet. The fantasy is that I’m the wholesome girl-next-door who’s secretly a freak. You’ll watch from the observation room. Don’t make a sound.”

She led him through a hidden door behind the bar, down a narrow hallway lined with small, dark rooms. One had a mirrored wall. She pointed him inside. “The glass is one-way. He tips extra for the ‘risk’. It’s part of the dream.”

The room was closet-sized, smelling of dust and old carpet. Through the glass, he saw a replica of a cozy, suburban bedroom—floral comforter, a lace lampshade, frilled pillows. It was a startling contrast to the club’s aesthetic. Brooke entered the room from another door. She had changed. Now she wore a simple, knee-length sundress and white Keds. Her hair was in a ponytail. She looked like she was about to host a backyard BBQ.

A moment later, the man entered. He was exactly as described: salt-and-pepper hair, a fit body in expensive casual wear, a watch that probably cost more than Jerome’s car. He smiled, a practiced, charming thing.

“Brooke. You look… delicious.”

“Hi, Mr. Henderson,” she said, her voice pitching higher, sweeter now. She clasped her hands in front of her. “I made lemonade. Would you like some?”

The performance was breathtaking. For the next hour, Jerome watched as Brooke constructed an elaborate, participatory fantasy. She was the naive neighbor girl, “accidentally” spilling lemonade on her dress, needing help out of the wet clothes, shyly revealing lingerie beneath. She gasped at the right moments, bit her lip with faux-innocence, whispered “gosh” and “gee” as the man’s hands explored her body.

She guided him, letting him believe he was in charge, while subtly directing every move. When he pushed her onto the bed, she turned it into a game of “strip checkers.” When he finally entered her, she cried out, “Oh my! It’s so… big!” with a convincing tremor of overwhelmed delight. She rode him with an expression of wide-eyed discovery, her sundress rucked up around her waist, her perfect, performed moans filling the soundproofed room.

Jerome watched, not exactly with arousal, but with a clinical fascination. He saw the mechanics of it. The slight shift in her eyes when she checked the clock on the nightstand. The way her breath hitched not from pleasure, but from the awkward angle. The seamless switch, as the man neared climax, to a whispered, filthy monologue about how she’d been dreaming of his “grown-up cock” all day, how she was his “dirty little secret.” It was a script, flawlessly delivered.

Afterward, as the man dressed, beaming with rejuvenated pride, she sat on the edge of the bed, the sundress back on, swinging her feet like a teenager. She listened to him talk about his golf game, nodding with rapt attention. He tucked a thick stack of bills into her Keds shoe by the door. A tip for the lemonade.

When the door shut, Brooke’s entire posture changed. The youthful buoyancy drained from her body. She stood, walked to the mirror—to where Jerome stood hidden—and looked directly at her own reflection. The face that looked back was tired, shrewd, and utterly empty of the character she’d just played. She gave a small, humorless smirk, then turned and left.

Jerome waited a full five minutes before exiting the observation room. He found her back in VIP 3, now in a silk robe, pouring a finger of actual whiskey into a glass.

“Well?” she asked, without turning.

“It was like watching a brilliant actor in a one-woman show,” he said.

She nodded, sipping the whiskey. “Exactly. And he left believing he was the star. That’s the art. Now…” She turned, her eyes sharp. “Your turn.”

“My turn?”

“You absorbed the theory. Now, practical application. I’m not your fantasy, Jerome. I’m your final exam. You’re not paying me. This is a critique.” She undid the tie of her robe, letting it fall open. She wore nothing underneath. Her body was a testament to a life fully lived—full, heavy breasts with dark nipples, a soft waist, hips that curved generously, the silvery stretch marks on her belly and thighs like maps of experience. She was powerfully, unapologetically real.

“Coco taught you technique. Bianca taught you aggression. Now I’m going to teach you audience awareness. You’re not fucking me. You’re performing for me. I am the critic. Your goal is to make me forget I’m critiquing. Make me believe in your fantasy.”

The challenge was clear. This was no longer about his need, his insecurity, his conquest. This was a test of skill, of empathy, of creation. He thought of what she’d said. They want to feel like they’re the only one.

He approached her, not with the predatory stride he’d used with Bianca, or the worshipful care he’d shown Coco. He moved with a quiet confidence, his eyes on hers, reading her. He stopped just before touching her.

“What’s the fantasy?” he asked, his voice low.

A flicker of surprise, then approval, crossed her face. “You’re a quick study. The fantasy is… the sincere enthusiast. The man who isn’t just using a body, but is genuinely, avidly obsessed with this body. This one. With the history written on it.”

He understood. He reached out, but not for her breasts or between her legs. His fingertips touched the stretch marks on her side, tracing their paths with a feather-light touch. “Tell me about this one,” he said.

She inhaled sharply. “What?”

“This line. It’s longer, deeper. Was that from the weight gain after Panama City? Or something else?”

A genuine, unscripted laugh burst from her. “Jesus. No one’s ever… Yeah. That one’s from a brief, disastrous marriage to a bass fisherman. I ate a lot of hush puppies.”

He smiled, a real one. He leaned in and pressed his lips to that specific stretch mark. Not a kiss of passion, but of interest. Of study. He worked his way across her belly, his mouth and hands exploring every curve, every mark, every slight imperfection. He paid attention to the texture of the skin on her inner thighs, slightly softer, to the way her breasts yielded to his touch with a satisfying weight. He narrated in a murmur, not with dirty talk, but with observations.

“You’re so soft here… This scar, is it from…?” “Childhood bike. No glamour there.”

He was building her a fantasy: that her lived-in body was a fascinating text, and he was the eager, dedicated scholar. He laid her back on the velvet booth, the material cool against her skin. He kissed down her torso, his tongue dipping into her navel, making her giggle, then gasp as he moved lower.

When he reached her pubic mound, he nuzzled the coarse hair, inhaling her scent—musky, clean, uniquely her.

“You smell like a woman who knows exactly what she wants,” he murmured, and felt her hips lift in response.

He didn’t dive in. He teased, using his tongue in slow, broad strokes, avoiding her clit, just learning the landscape of her folds. She was wet, her arousal a tangible, slick heat. He slipped a finger inside her, curling it, finding a rhythm that made her back arch. He added a second finger, stretching her gently, his mouth still working with a lazy, devoted attention.

“You’re so tight here,” he whispered against her thigh. “And so hot. You’re fucking blazing inside.”

“Stop talking and make me come, you thorough bastard,” she groaned, but there was a smile in her voice.

He finally zeroed in on her clit, sucking the hard little bud into his mouth, applying a firm, steady pressure. He fucked her with his fingers, his palm grinding against her as he worked her with his tongue. He listened to her breathing, felt the tension coiling in her thighs, and adjusted his pace, building her slowly, steadily, toward the edge.

Her orgasm wasn’t a scream, but a deep, guttural series of curses that shook her entire frame.

“Fuck! Oh, fuck yes, right there, goddamn…” She clenched around his fingers, her juices coating his hand. He rode it out with her, gentling his tongue until she pushed his head away, oversensitive.

Before she could recover, he was on her, his cock pressing against her soaked entrance. He looked her in the eyes. “I need to be inside this history. All of it.”

She nodded, breathless, her critic’s facade utterly shattered. He pushed in, a slow, profound invasion that made them both groan. She was incredibly tight, a velvet fist gripping him. He didn’t move immediately, just let her feel his full length, let himself savor the incredible, hot clasp of her.

“You feel like a fucking revelation,” he breathed, and began to move.

This was not a frantic, pounding fuck. It was a deep, rolling, intense grind.

Every thrust was a deliberate claim, a deep, rolling, intense grind that sought not just friction but fusion. He kept his eyes locked on hers, watching the critic fade with each drive of his hips, replaced by raw, unfiltered sensation. Her breath hitched in staccato gasps that synced with the wet, rhythmic slap of their joining.

“You like that, don’t you?” he grunted, his voice thick. “You like feeling how much I want this specific pussy. This one.”

“God, yes,” she hissed, her nails digging into his back. “Talk to me. Keep talking to me.”

“It’s so fucking deep. I can feel you clinging to me. Trying to keep me inside.” He shifted, angling his hips, and she cried out as he brushed a spot that made her vision whiten. “There. Right there. You’re gonna come on this cock again. You’re gonna soak it.”

She was unraveling beneath him, her composure shredded. “Make me. Please.”

He pistoned into her, abandoning the slow grind for a harder, faster pace. The booth creaked in protest. He fucked her with a focused brutality that was both learned and instinctual, each impact driving a choked sound from her throat. Sweat dripped from his chin onto her chest, mingling with the scent of her perfume and their sex.

“I’m close,” she warned, her heels locking at the small of his back. “Don’t stop. Don’t you fucking stop…”

He wouldn’t. He couldn’t. The coiled tension in his balls was a screaming demand. He reached between them, his thumb finding her swollen clit, and rubbed hard, fast circles.

“Come,” he commanded, his own control fraying. “Do it now.”

Her body bowed off the velvet, a silent scream on her lips as the orgasm detonated. She clamped around him in violent, rippling spasms, a wet, rhythmic vise that milked him relentlessly. The feeling tore through his own restraint.

“Fuck! Brooke!” His own release was a white-hot surge, pulsing into her in thick, claiming ropes. He buried himself to the hilt, grinding as he emptied every drop, his muscles trembling with the force of it.

They collapsed together, a slick, breathing tangle in the dim booth. The only sounds were their ragged breaths and the distant thump of bass from the main club, a world away. He felt spent, hollowed out, but strangely clear.

After a long moment, she patted his shoulder. “Okay. Off. You’re heavy.”

He rolled to the side, extracting himself from her warmth. The cool air hit his wet skin. They lay side by side, staring at the stained ceiling.

“Well?” he finally asked.

She lit a cigarette, the flame briefly illuminating her satisfied, pensive face.

“You passed. With notes.” She exhaled a plume of smoke. “You read the room. You built the narrative. You made it about my body, not your dick. That’s advanced shit. Most men just jackhammer away, trying to prove a point to themselves.”

“What are the notes?”

“The transition from scholar to beast was a little abrupt. Work on the seamlessness. The best performances feel inevitable, not like scene changes.” She took another drag. “But your dirty talk is good. Specific. It shows you’re paying attention. That’s the real currency.”

She sat up, reaching for her robe. “Thursday. Serena’s play. You understand what you’re walking into now? You’re not just holding film. You’re becoming part of the fantasy they sell to Eckles. The fantasy of control, of seamless operations.”

Jerome sat up, pulling on his clothes. The clarity was morphing into a cold, sharp focus. “I’m the new product. Proof of their adaptability.”

“Bingo.” She tied her robe, her professional demeanor reassembling itself piece by piece. “Michael’s fantasy is that he’s the master puppeteer. Your job is to make Eckles see Michael as a messy, loose string. And to make Serena look like the only one with scissors.” She stubbed out the cigarette. “Bill’s fantasy is smooth operations. Bianca’s is that she’s above it all. Coco’s is that she’s essential. Everyone’s got one.”

“And yours?” he asked, buckling his belt.

She smiled, but it didn’t reach her eyes.

“My fantasy is that this,” she gestured around the VIP booth, “is just a side gig. That the real me is at those garden parties, selling three-bedroom colonials with good schools. The truth is, this is where I’m most real. The rest is just a better-quality costume.” She stood. “Remember that. The fantasy is armor. For everyone. Your job on Thursday is to figure out whose armor is the thinnest, and push right the fuck through it.”

She left him there, the scent of sex and smoke hanging in the air. He walked out past the dark stage. Bill was gone, the money counted and secured. The club was a hollowed-out shell.

His phone buzzed in the silent cavern. A message from Bianca. It was a picture. A blurry, dark shot of Michael, outside a sleek downtown building, talking urgently on his phone. The time stamp was twenty minutes ago. The building’s discreet plaque was readable: City Planning Commission, Suite 1200.

Under the image, her text: He’s not waiting for Thursday. He’s making his own delivery.

The cold focus ignited into adrenaline. Michael was moving early, trying to cut the legs out from under Serena’s presentation. Jerome’s hand went to his pocket, feeling the solid shape of the encrypted drive. The fantasy was crumbling before the performance even started.

He typed back: Where are you?

Her response was immediate: Outside. In the alley. Hurry up.

He pushed through the club’s back door, the afternoon sun glaring after the perpetual twilight inside. Bianca was leaning against her car, a beat-up muscle car that didn’t suit her yet somehow perfectly did.

“Get in,” she said, her face grim. “We have to find Coco. Michael just went to see Eckles with a ‘file.’ Serena’s off-grid, prepping for some donor lunch. We’re the only flank he didn’t account for.”

Jerome slid into the passenger seat, the leather hot from the sun. “What’s in the file?”

“If it’s what I think, it’s not just the ledger. It’s photos. Of Lana. From after.” Bianca started the car, the engine roaring to life with a violence that matched the look in her eyes. “He’s not just threatening exposure. He’s trying to disgust Eckles into pulling support entirely. A moral crisis is better leverage than a financial one.”

She peeled out of the alley, the tires screeching. “Coco’s the only one who knows where the originals are. The only one who can prove what they really are. We need to get to her before Michael figures out she’s the linchpin.”

The city blurred past the window. Jerome’s mind raced, connecting wires. Brooke’s lesson about armor. Michael’s was the aggrieved moralist. Eckles’ was the discreet power broker. One fantasy was about to crash into the other.

And he and Bianca were speeding directly into the collision.

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