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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 3: Dolla Bill

The encrypted message sat in his phone like a live grenade. Jerome didn’t reply. Instead, he followed Coco’s instruction, meeting her outside a nondescript door tucked between a shuttered bodega and a nail salon in a part of the city that pulsed with a different, grimier rhythm. The sign above the door was just a flickering, blood-red neon outline of a high heel.

“Remember,” Coco said, adjusting the collar of his jacket. She was dressed in a powerful burgundy pantsuit, looking every bit the elegant auntie, utterly out of place. “This is a field trip. You observe. You listen. You keep your wallet in your front pocket and your judgments to yourself. Bill is an acquaintance from a lifetime ago. He’s not a good man, but he’s a clear-eyed one. He sees the game for what it is.”

She knocked—a specific rhythm. A slit in the door opened, then closed. A series of deadbolts clanked, and the door swung inward.

The sound hit first. A deep, subsonic bass that vibrated in Jerome’s molars, overlaid with the tinny shimmer of a synth track. The smell was next: spilled liquor, industrial cleaner, cloying body spray, and underneath it all, the sharp, animal scent of sweat. They were in a narrow hallway that opened into the main room of Dolla Bill’s.

It wasn’t a large club, but every inch was engineered for twilight intimacy. Velvet booths, the color of bruised plums, lined the walls. The lighting was a perpetual dusk, with pinspots following the figures on the central stage and a lazy disco ball scattering fractured light like broken glass. On stage, a woman moved with a hypnotic, weary grace, her body a series of perfect, practiced curves under the hot white light.

Coco led him past the main floor, nodding at a mountainous bouncer who unhooked a velvet rope. They ascended a short flight of stairs to the VIP section. It was quieter, the booths deeper, the tables scarred by rings from a thousand glasses. In the largest booth, a man held court.

Dolla Bill was a paradox in a silk cream-colored suit. He might have been sixty, his face a road map of hard living and shrewd calculation, but his eyes were a vivid, alert amber. A heavy gold chain rested on his chest. He held a smoking cigar in one hand; the other rested proprietorially on the thigh of a young woman who sat beside him, her expression vacant as a screen saver.

“Coco,” he said, his voice a gravelly rumble that cut through the music. He didn’t smile. “Been a minute. A longgggg minute. You bringin’ me fresh talent or you just slummin’ for old times’ sake?”

“Neither, Bill. This is Jerome. A friend. He’s getting an education.”

Bill’s amber eyes slid to Jerome, appraising him with the speed of a barcode scanner. “Software. Good watch. Nervous hands. Ain’t never been in a place like this ‘cept in his browser history.” He chuckled, a sound like gravel in a tin can. “Sit. Education costs. First drink’s on the house. After that, you pay.”

Jerome slid into the booth opposite him, Coco beside him. A server appeared instantly—a woman with eyes that didn’t quite meet theirs. Bill gestured, and two whiskeys materialized.

“Coco says you’re learnin’ the ways of the world. The flesh trade.” Bill took a slow pull of his cigar. “This here is the factory floor. All that poetry them other women been feedin’ you? This is the fucking translation of all of it. Ain’t nothin’ to it but product and price.”

As if on cue, a few women drifted toward the booth. They were all stunning, each in a radically different way—one a tall, statuesque redhead, another a petite Asian woman with eyes like black chips of obsidian, a third with curves that defied physics. They smiled, but it didn’t reach their eyes. They were waiting for an order.

“This is Chloe, Lexi, and Diamond,” Bill said, waving the cigar. “Top shelf talent. They’ll give you a private dance. Show you some tricks. For a fee. Or, you can just talk. That costs, too. Time is money, kid. Everything is money.”

Jerome felt a cold clench in his gut. This was the underbelly Coco had hinted at. The transaction, stripped of all pretense of connection. “

I’m just here to listen,” he managed.

Bill laughed. “Smart man. First smart thing you said. Listen up, then.” He leaned forward, the gold chain swinging. “See, all them beautiful women out there, they got a currency. This one—” he jerked a thumb at the woman beside him, who didn’t flinch, “—her currency is obedience. She does what she’s told, she gets protected. The girls on the floor, their currency is fantasy. They sell a dream that ends when the song does. Your lady friends, the ones teachin’ you? Their currency is power. They take what they want, give what they choose. That’s an even rarer market. A dangerous one.”

He pointed his cigar at Jerome. “You walkin’ between markets, kid. You gotta know the exchange rate. A woman who sells a dream will fuckin’ bankrupt you. A woman who sells power will eat you alive if you’re weak. And a man,” he said, his eyes glinting, “Who thinks with his little head instead of his big one ends up workin’ for me, or face-down in a gutter. There’s no romance here. Just logistics.”

Jerome’s whiskey tasted like ash. He watched as Chloe, the redhead, led a sleek-looking man in a business suit toward a curtained alcove. The man’s hand was already on her ass, gripping possessively. She glanced back once, her eyes meeting Jerome’s for a split second. He saw no invitation there, only a profound, hollowed-out resignation.

“He’s not ready for the talent, Bill,” Coco said softly, but firmly.

“Maybe not. But he needs to see it.” Bill snapped his fingers. “Bianca! Come say hello.”

From behind the long, glowing bar that anchored the room, a woman looked up. She had been polishing a glass with a focused intensity. She was strikingly beautiful, but in a way that seemed to reject the room’s aesthetic. Her hair was braided back in intricate, severe cornrows. She wore a simple black tank top that showed off toned arms covered in delicate, meaningful tattoos. Her face was all high cheekbones and a full, unsmiling mouth. Her eyes, when they landed on Jerome, were like a physical impact—dark, intelligent, and blazing with undisguised skepticism.

She put the glass down and walked over, moving with the fluid, efficient grace of a fighter. She didn’t look at Bill.

“This is Bianca. Best damn bartender in the city. And the only person in this building who doesn’t work for me. She rents the bar. Don’t piss her off.”

Bianca’s gaze swept over Jerome, then Coco. “Coco. You vouching for this?”

“I am.”

“Hmph.” Her eyes locked back on Jerome. “You look lost.”

“I’m… getting oriented.”

“This ain’t a place you get oriented. This is a place you get lost or you get got. Which one you plannin’ on?” There was no malice in her voice, just a brutal, weary honesty.

“I’m just here with my friend,” Jerome said, gesturing to Coco, finding a sliver of his newfound spine.

Bianca’s expression softened, just a fraction. “Then you should probably leave. The air in here rots good sense.” She gave Coco a slight, almost imperceptible nod, and turned back to the bar.

“See?” Bill said, exhaling a plume of smoke. “Treachery. She’s treacherous ‘cause she’s brutally honest. That’s the most dangerous kind. Now,” he said, standing. “You wanted to meet the talent. Come on. Let’s go.”

He led Jerome and Coco through a concealed door, down a narrower, dimmer hallway lined with several doors. Behind one, Jerome could hear the business suit man grunting, a steady, rhythmic slapping sound, and the flat, performative moans of the woman, Chloe. Bill didn’t pause. He stopped at the last door, opened it without knocking.

It was a small, bland room. A vinyl sofa, a mini-fridge, a floor lamp. Diamond, the woman with the impossible curves, was there, touching up her makeup in a mirror. She wore only a glittering G-string and pasties.

“Diamond. This is Jerome. He’s a student. Give him the standard intro. Fifteen minutes.” He looked at Jerome. “This is the curriculum. You watch. You learn what $500 buys you. And you keep your hands to yourself unless she says otherwise.”

Bill and Coco stepped back into the hall, closing the door. Jerome was alone with her. The music was muffled here, a distant throb.

Diamond turned from the mirror. Her smile was a professional fixture.

“Hey, baby. You want a dance? Or you wanna talk?”

The clinical, hollow feeling was overwhelming. This wasn’t Serena’s challenging gaze or Coco’s warm guidance. This was a service. He thought of Michael’s message, of the photo. Of being a pawn in someone else’s game. A strange, defiant clarity cut through his discomfort.

“What do YOU want?” he asked her.

Her smile flickered, just for an instant. “Want?”

“Yeah. If you weren’t here. What would you want?”

She laughed, a short, brittle sound. “Honey, ain’t nobody paid to hear that. You paid for fantasy. You want the virgin or the slut? The girlfriend or the freak? I do ‘em all.”

“What’s the realest one?” The question came out before he could stop it. He was using the language Coco had given him—looking for the true story.

Diamond studied him. The professional veneer didn’t crack, but it thinned. She walked over, her hips swaying not with seduction, but with a tired efficiency. She stood before him, so close he could smell the vanilla of her lotion and the underlying tang of someone else’s sweat.

“The realest one…” she said, her voice dropping, “Is the one where you understand this is a job. I grind on your dick, you eventually come in your pants, I go wipe off the glitter and count my money. That’s it. No fairy tale. No connection. Just biology and business.” Her eyes were hard. “That what you want to learn?”

He nodded, silently.

“Alright then. Sit.”

He sat on the edge of the vinyl sofa. She didn’t turn on music. The only sound was the hum of the mini-fridge. She stood over him, then slowly, with a dancer’s control, lowered herself to her knees. Her hands went to his belt.

“This part is about access,” she said, undoing the buckle, the button, the zipper. Her fingers were cool. “You pay for the access.” She pulled his cock out. It was half-hard, confused by the lack of passion. “This part is about function.” She spit into her palm, a coarse, unceremonious act, and began to stroke.

Her grip was firm, practiced, utterly devoid of affection. The spit provided a slick, cool glide that felt nothing like Serena’s wet heat or Coco’s generous warmth. Jerome watched, detached, as his body responded to the mechanical stimulation. His cock hardened in her fist, a simple biological betrayal.

“See?” Diamond said, her voice a monotone over the rhythmic sound of her hand. “It’s just a pump. Input, output. No mystery.” She increased her pace, her other hand cupping his balls, rolling them with a clinical precision. “You could be anyone. I could be anyone. That’s the point.”

Jerome felt a revulsion that had nothing to do with her. It was for the entire theater of it, for the reduction of something that, with Serena and Coco, had felt like a terrifying and profound language into this… binary code. Pleasure detached from person. He thought of Coco’s stretch marks, maps of a life. This was a blank screen.

“You gonna come?” she asked, not looking at his face, her eyes on her working hand. “I can make you. It’s what you paid for.”

That was the trigger. The word. Paid. It wasn’t the greed that sickened him, but the sheer, barren honesty. He placed his hand over hers, stilling it. Her eyes flicked up, wary.

“Stop,” he said. His voice was quieter than he intended.

She released him instantly, sitting back on her heels, her expression shifting to one of mild, professional concern. “Not what you wanted? I can do something else. A dance. Talk.”

“No,” Jerome said, tucking himself away with fumbling fingers. The ache of denied release was a dull throb. “It’s exactly what I needed to see. Thank you.”

She blinked, the script broken. Nobody thanked her. She stood, smoothing her G-string. “Your time’s almost up anyway.”

Out in the hallway, Bill leaned against the wall, smoking. Coco stood beside him, her face unreadable.

Bill pushed off the wall, the amber eyes dissecting Jerome’s expression.

“So? You get your money’s worth, college boy? Learn the difference between a woman and a product?”

“I learned the difference between a transaction and a conversation,” Jerome said, his voice steadier than he felt. The ghost of Diamond’s mechanical hand still tingled on his skin, a vulgar echo.

Bill’s laughter was a short, approving bark. “Good. Remember that shit. These other niggas can’t tell.” He flicked ash onto the stained carpet. “Now, the real lesson is this: You walk outta here, you gonna want somethin’ real. Your dick’s confused. It got the service, but it didn’t get the spirit. That’s when a smart man makes a bad choice. He goes lookin’ for a cheap connection to wash the taste out his mouth.”

He gestured with his cigar back toward the main floor. “That’s when you get got, my boy. You vulnerable. The wolves smell it.” His eyes drifted meaningfully toward the bar, where Bianca was slicing limes with violent precision. “Or you find a wolf who’s honest about her teeth.”

Coco finally spoke. “You’ve shown him the factory floor, Bill. That’s enough.”

“Ain’t my factory,” Bill said, holding up his hands. “I just provide the venue. The girls are all independent contractors. The treachery is all theirs.” He leaned close to Jerome, the smell of cigar and expensive cologne enveloping him. “But since Coco vouches, I’ll offer you a job. Not with the talent. Security camera maintenance. My system’s a patchwork bitch. You’re a software guy. You could untangle it. Pays cash. Lets you see the whole operation from the eyeball in the ceiling. Best education there is.”

The offer hung in the stale air. Jerome looked at Coco. Her slight, almost imperceptible nod was the only sign she hadn’t expected this.

“I’ll think about it,” Jerome said.

“You do that.” Bill clapped him on the shoulder, a gesture that felt like a transaction itself. “Now get the fuck out of my office. I got business to handle.”

Back in the VIP lounge, the bass felt like a physical pressure. Jerome’s head throbbed. He needed air, light, anything to erase the feeling of vinyl and cold hands. Coco touched his arm.

“I need a minute,” he said, and made his way toward the bar.

Bianca saw him coming and didn’t smile. She poured two fingers of whiskey into a fresh glass and slid it to him before he could speak. “On the house. You look like you seen a ghost.”

“Feels like I talked to one,” he said, taking the drink. It burned, clean and honest. “A very expensive ghost.”

“Diamond,” Bianca stated, wiping the bar. “She’s the best at what she does. Which is making you feel nothing at all. That’s what most of them want, you know. To feel nothing.”

“What do you want?” The question slipped out again, the same one he’d asked in the back room.

She stopped wiping, fixed him with that dark, unflinching gaze. “Right now? For my shift to end. For this damn song to change. For men to stop thinking their dick is a compass.” She shrugged. “Simple things.”

He laughed, a raw, surprised sound. “You’re not like anyone here.”

“And you’re a tourist holding a map upside down.” She leaned on the bar, her voice dropping. “Coco’s a good woman. She sees potential. I see collateral damage. You’re swimming with sharks, baby. And you still think you’re at the aquarium.”

“Michael,” Jerome said, the name feeling dangerous on his tongue here.

Bianca’s eyes narrowed. “Serena’s problem. And now yours, apparently. I don’t do drama. I pour drinks.” She looked past him, her expression shifting. “But if you’re gonna swim, learn the current. Bill’s offer? The camera job? It’s a trap and a gift. You’ll see everything. And everything will see you.”

Jerome finished his whiskey. The synthetic heat of the alcohol coiled in his stomach, but it couldn’t reach the cold knot left by Diamond’s hollow eyes and Bianca’s blistering truths. He needed to feel something real, something that wasn’t a performance or a warning. The charged space between him and the bartender crackled with a friction that promised, at least, authenticity.

“When does your shift end?” he asked, the words a low vibration in his chest.

Bianca’s smirk held no warmth, only a sharp curiosity. “Ten minutes. You gonna wait? Or you gonna run back to your safe little tutorials?”

“I’m done with safe.”

Ten minutes later, they were in the alley behind the club, a canyon of grime and dumpsters under a sickly yellow security light. The club’s thump was a muffled heartbeat through the bricks. Bianca leaned against the graffitied wall, pulling a pack of cigarettes from her jeans.

“So? What now, tourist? You want some deep conversation about my tragic past?”

Jerome took the cigarette from her lips before she could light it and tossed it into a puddle. “No.” He moved into her space, caging her against the wall. The smell of her was citrus and salt, a shocking cleanliness after the club’s sweet rot. “I want you to be as real with me as you were at the bar.”

She laughed, a short, harsh sound. “Real? You can’t handle my real.” But her eyes dropped to his mouth, and a challenge flared in them. “My Real is messy. My Real is impatient.” Her hand snaked down, palming him roughly through his jeans. He was already hard, a throbbing ache from the frustration of the back room. “Mine… doesn’t ask for permission.”

He grabbed her wrist, not to stop her, but to press her hand harder against himself.

“Then show me.”

She unbuttoned his jeans with efficient, ruthless tugs. The cold alley air hit his skin, followed by the sear of her hand wrapping around his bare cock. Her grip was nothing like Diamond’s. It was demanding, possessive, a claim staking.

“This what you wanted? To fuck the angry pissed off black girl in an alley? Get your dick wet with something authentic?”

“Yes,” he grunted, the truth of it raw and ugly.

“Then shut the fuck up and get to work.” She shoved her own jeans and underwear down her hips, just enough. She didn’t guide him. She simply spread her legs, a dark invitation in the shadows, and pulled him close by the back of his neck.

He drove into her in one deep, claiming stroke. She was hot and tight and shockingly wet. Her head slammed back against the brick.

“Oh, fuck,” she hissed, her professional composure evaporating into something purely feral.

He set a punishing rhythm immediately, each thrust a battering ram against the evening’s lessons. This was no symphony. This was a complete street fight. The slick, filthy sounds of their coupling filled the alley, mixing with the distant sirens and the dumpster stench. Bianca met every drive with a roll of her hips, her teeth finding his shoulder, biting down through his shirt.

“That’s it,” she panted in his ear, her voice gritty. “No sweet shit. No lessons. Just fuck me. Fuck the memory of that plastic ass stripper bitch right out your head.”

He pistoned into her, his hands gripping her ass, lifting her to take him deeper. The vulgarity of it, the public risk, the sheer unvarnished hunger, unraveled him fast. His climax built like a storm surge, blunt and inevitable.

“I’m gonna come,” he warned, his voice strained.

“Do it,” she growled, clawing at his back. “Come in me. Mark it real, you motherfucker.”

The permission, filthy and direct, snapped the last thread. He slammed home and exploded, a raw, guttural shout torn from his throat as he pulsed inside her, pouring out the tension, the confusion, the hollow transaction into her willing, heated flesh. He shook with the force of it, his forehead against the cool brick beside her head.

For a moment, there was only the sound of their ragged breathing. Then, with a practicality that was its own kind of violence, she pushed him off her. She pulled her clothes up, adjusting her tank top. He fumbled with his jeans, his body humming, his mind eerily quiet.

She lit her cigarette finally, the flame illuminating her face—now closed off, impenetrable once more. “

Congratulations,” she said, smoke curling from her lips. “You just had your first real fuck in the city. Now you’re in the game for real.” She turned to walk away, then paused. “Check your phone.”

He pulled it from his pocket. The screen glowed in the alley’s gloom. Another encrypted message.

The curriculum is corruption. She’s making you a customer. I can show you the receipts. Meet me. Tomorrow. 3 PM. The botanical gardens, temperate greenhouse. Come alone. - M

Bianca watched him read it, her expression knowing. “The current just got stronger, tourist.” She dropped the cigarette, crushed it under her boot, and vanished around the corner, leaving him alone with the smell of sex and garbage, and a choice that now felt like a knife pointed at his own throat.

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