[CC] The Gentleman And The Whore

NSFWConstructive Criticism

This was based on a prompt about a society where semen is a valuable resource and a man is robbed. The original post was removed or deleted, but since I wrote a story I quite like, here it is.

Late night in the city, cool and quiet, a light mist of rain falling, barely visible except in the orange halos of the gas lamps. He walks quickly, his head down, footsteps echoing off the cobblestones, a tall, lean figure in a topcoat and slacks, shoulders hunched, hands in his pockets.

They watch from the shadows, pressed against walls, crouched behind boxes, tense with anticipation, waiting for the signal, waiting for her.

The man rounds a corner to find her leaning against the wall, smoking a cigarette. She's perhaps a foot shorter, barely a hundred pounds, in a light coat, an old sweater, and fingerless gloves, a plaid skirt that flutters around her bare thighs, knee-length socks, and shoes that have seen better days. A flat cap is pulled down low over her eyes, dirty blonde hair poking out from beneath it.

"Evening, mister," she says, exhaling a plume of smoke.

"Good evening," he says, with a tight smile, passing her without breaking stride.

She pushes off from the wall and falls into step a few feet behind him. He swallows, glancing around, increasing his pace.

"Where are you headed in such a hurry?" she asks.

"Home," he mutters.

"To the wife?"

He stops, turns to face her. "Yes," he says. "Now if you don't mind…"

"Don't mind what?" She's smiling, her mouth the only part of her face that isn't in shadow.

"Don't mind leaving me be. I'm just trying to get home."

"Where've you been? Got a mistress?"

"No. Not that it's any of your business. Excuse me."

He turns to walk on. Further down the street, several other girls have gathered. They're watching him, arms folded.

"Dangerous to be alone out here at this time of night," the girl in the flat cap says. "I could walk you home, if you like. Make sure you get there safely."

"I…" He looks around. There's never a policewoman when you need one. "Okay."

"There will, of course, be a small fee. But judging by those nice clothes you're wearing, I'd guess you're a big tipper."

She approaches him, slowly removing one of her gloves, tucking it into a pocket. The top of her head barely reaches his chest when she stands before him, and the absurdity of it, this slip of a girl, young enough to be his daughter, robbing him in plain sight, angers him enough that he considers just shoving her to the ground and making a break for it.

But the other girls are watching, and he's sure that's not all of them. He may have been stupid enough to try and make this trip alone, but he's smart enough not to compound that mistake.

Flat Cap undoes the bottom buttons of his top coat, presses her hand against the crotch of his pants, squeezes. Despite himself, he feels a stirring in response, and when she unzips his fly and reaches inside, cold fingers pulling down his underwear and then curling around his cock, he's beginning to get hard.

"Lucky wife," she says, glancing down as she takes him out, right there in the street.

She begins to stroke him, slowly at first, her hand gentle and skilful. In moments, he's fully erect, breathing steadily, awkwardly shifting his weight from foot to foot, unsure what to do with his hands, where to look.

She laughs quietly. "Some guys take it personally, get all ashamed. It doesn't have to be like that."

"No?" There's a tremor in his voice.

She looks up at him and he's startled by how young she is, how beautiful. She has tired eyes of a washed out green, a scattering of freckles across the bridge of her nose and her cheeks, and that smile, defiance and amusement at once, is enough to knock any man off balance.

"Guess how old I am, she says.

"I don't know."

Her grip tightens around his cock, her hand moving a little quicker. He groans.

"Guess," she says.

"Eighteen," he manages.

"Nineteen," she says. "I mean, that's gotta be a fantasy, right? Barely legal girl on your dick?"

"I'm married."

"But you know the score. I'm sure wifey does, too. You've got something I need, mister. It's not like you're out here cheating."

"Please stop," he said. "There must be something else. My coat or my watch, something."

"Please. You think if I fenced clothes I'd be wearing this shit?" She pulls at the hem of her sweater, briefly revealing several inches of her flat stomach.

He looks down. He can't help it. And she notices. Of course she does.

"It's okay," she says. "Tough not to think with your dick at a time like this, right?

She's putting a little twist in each stroke now, and he can feel himself beginning to lose his self-control.

"Please…" he says again, breathing hard, voice shaking. "Oh, god."

"That's it. Come for me, mister. Give me a nice big load."

She's flushed, and he can see the tips of her nipples through her sweater.

"You're...enjoying this."

She laughs and shrugs, a little you got me gesture that's somehow sexy and sweet at the same time. Knowing she isn't wearing a bra, he wonders if she wears panties, and that leads quite naturally to a flash of a fantasy, pushing her up against the wall, pulling up her skirt.

She reaches into her pocket with her free hand, pulls out a vial, uncorks it with her teeth, and with impeccable timing, places the open end over the tip of his cock as he groans again and a thick spurt of come shoots straight into it. She gently, expertly squeezes his shaft as it pulses in her hand, until the vial is about half full and he's done, breathing hard, sweat standing out on his brow.

"Thank you," she says, her hand pushing back into his underwear, cupping his balls. "But I think you can do better."

The girls from down the street have moved up behind him, and now - as one - they grab him. He gives a surprised yelp, but by the time he begins to struggle, he's already been overwhelmed, a hand clamped over his mouth, others holding his arms, dragging him off the street and into an alleyway. Flat Cap drops the vial in her pocket, looks both ways, then follows. She's whistling.

Halfway down the alley, behind a dumpster that shields it from the street, is a dirty mattress. The girls, none of them older than twenty, push him down onto it and set about him, two of them pinning his wrists to the mattress and another covering his mouth with her hand as they open his coat and his shirt, pull his pants and underwear down around his thighs.

Flat Cap watches as she takes off her jacket and drapes it over the dumpster. He struggles desperately, but while he's easily a match for any of the girls individually, there are now five of them holding him down.

"We're not going to hurt you, mister," she says. "I just hate to leave a heist without taking all the goods, you know?"

She stands over him, feet to either side of his waist, and he realizes he can see up her skirt. She really isn't wearing any panties. His cock twitches and the girls laugh.

"Jerking you off got me all wet. Do you want to stick your tongue in my honeypot?"

He gives a muffled moan of protest, but she isn't waiting for an answer, anyway. She plants her feet to each side of his head, then gets down on her knees, and the girl with a hand over his mouth pulls it aside as he gets a close-up view of her splayed pink pussy, flesh glistening with arousal, before she grinds it against his face, pushing her hands through his hair, riding him like she's fucking him.

"Open your mouth, darling. Give me that tongue," she says, slightly breathlessly.

There are hands on his cock and his balls, he can't even tell whose, squeezing and stroking his tender skin, and he opens his mouth to her cunt, her desire inflaming him, his tongue parting her labia, tasting, her scent filling his nose and mouth as he finds the fleshy hood of her clit and laps hungrily at it. He feels her hands closing on his hair, pulling herself down, wanting more, her thighs twitching and shaking.

He's hard again, his hips lifting off the mattress, straining upward as a girl he can't see takes him in her mouth, wet heat, her lips pulling tight to his skin, her tongue dancing over him, teasing and caressing.

"Give me his hands," Flat Cap says, her voice a moan.

They let go of his wrists and she grabs his hands and pulls them up under her sweater, onto her small, soft breasts. He squeezes them hard, pinches her swollen nipples, his tongue aching, working relentlessly at her clit.

"I'm gonna come," she breathes. "I'm gonna fucking come."

She pushes down hard on his face. He can feel her shaking, feel the rhythmic tensing of the muscles in her thighs and her abdomen. He twists her nipples and she gives a little yelp then suddenly inhales and holds it, her whole body rigid as her orgasm peaks and then the breath rushes out of her in a sob and she has to lift herself off him, gasping.

He raises his head, his face smeared with Flat Cap's arousal, sees a chubby girl with a pretty face and short, jet black hair devouring his cock, her head bobbing quickly up and down. Another girl, a blonde, her face mostly obscured, is licking and kissing his balls. The others watch, rapt and excited.

It's too much. All of it. He bites his lip as he reaches his second climax, and he watches the black haired girl fumble a vial from her pocket as he comes in her mouth. She raises her head and spits into it. The last of his orgasm drips down the side of his cock, and the other girls scramble for it, scooping the precious fluid up with their fingers.

"Go on," Flat Cap says to them, "Fuck off. He's done."

They're gone as quickly as they appeared, scrambling to their feet and running off down the alley, leaving him alone with Flat Cap.

"Eat your wife's cunt like that?" she asks.

He begins to pull his pants and underwear up, and she stops him with a hand on his wrist.

"How about the mistress?"

"I don't have a fucking mistress."

"Do you want one?"

He looks at her. She's propped up on one elbow, not quite touching him. She isn't smiling.

"You just robbed me," he says.

"You were into it."

"I...my wife would kill me if she knew about this. The police would laugh me out of the station."

"So don't tell them. Meet me here, say once a week. I'll do all the things your wife won't, anything you want, and I get to keep the results."

"You're insane. No."

Her hand moves from his wrist to his cock, her touch feather light, fingertips just barely making contact with his skin, tracing a path along his shaft, around the head.

"Tell me what you want, mister," she says, her voice low. "Do you want to fuck me?"

"No."

"Liar."

"I...stop."

"Do you feel humiliated? Angry? Wanna get me back? Bend me over and fuck my tight little pussy till I beg you to stop?"

Somehow, he was starting to get hard again, letting her stroke him, his eyes going down to where the hem of her skirt sat high on her thighs.

"Does your wife let you fuck her ass? I'll let you. I'll let you fuck my ass right now. Come on, mister, you can warm me up with your fingers and that dirty fucking tongue of yours, then I'll play with myself while you pound my asshole."

"Stop saying those things!"

"Put something in my mouth." She grins.

Later, he was sure that he meant to push her off him, pull up his pants, and get to his feet, maybe take the long way home to walk off the shame he felt, maybe sit in his study and drink a glass of whiskey until he could sleep. Instead, he finds himself shoving her down on her back, slapping her hat off her head, pinning her wrists as his had been pinned, straddling her shoulders, forcing his cock into her mouth.

He thrusts between her slack lips as he'd briefly imagined thrusting into her cunt, driving his swollen cock back into her throat, making her gag on it, her eyes watering as he moves his hips, hard and fast, the motion punctuated by the sound of her choking on him, saliva dripping from her lips, wet strings grabbing at his skin.

It isn't enough. He pulls out, flips her easily onto her front, hears her spit and weeze laughter as he flips up the back of her skirt.

"You want it in your ass, you little whore? Huh?"

"Give it to me. Fuck my ass."

He pulls her back to him, up onto her knees, her head and chest still down on the mattress. He pushes her legs apart so she's spread for him, her pussy and the dark pink flesh of her asshole.

"Fingers in your mouth and then in your hole. Show me you want this cock," he says.

She does as she's told, two fingers in her mouth and then reaching back, pushing them into her ass, working them back and forth as he watches, stroking himself.

"Now touch yourself. Rub that little clit. You're gonna come for me."

She pulls her fingers free, and as she moves them to her pussy, he replaces them with his cock, pressing against the tightness of her hole, and then in, groaning at the grip of her, taking hold of her hips as he begins to fuck her.

He thinks of how they humiliated him, how she humiliated him. How they held him down, how she rode his face. He digs his fingers into her soft skin and fucks her harder than he's ever fucked a woman in his life, taking pleasure in the sound of her moans and the rapid, meaty slaps of his body meeting hers, feeling her frantically masturbating as he drives his cock into her over and over.

She comes again, pushing her ass back to meet him, quivering, but he has no intention of stopping, and when she falls forward to lie flat on her front, exhausted, he goes with her, grabs a fistful of her hair, puts his mouth to her ear as he continues to fuck her.

"You're not getting this," he says, his breathing labored. "You hear me?" "You're...not...getting...this."

He gets off her, pulls her up by her hair, and brings her face back down to his crotch, filling her mouth with his cock again as he reaches his third orgasm. Even in the midst of this, he sees her hand go to her pocket, and he holds her head where it is as he comes in her mouth.

"Swallow it," he says, pushing as far into his throat as he can, balls deep in her mouth.

She gags, her eyes rolling back in her head, then swallows convulsively. The hand comes out of her pocket and she taps his stomach. It takes him a moment to recognize the gesture, but he releases her, watches her fall back, gasping.

They watch each other, regaining their breath and their composure. She wipes her mouth, reaches for the hat and jams it back down on her head as he finally pulls up his pants and buttons his shirt.

"First one's mine," he says finally. "Anywhere I want. After that, whatever else you can get out of me, you can keep."

She shakes her head, getting up. "First one's always the good stuff. I get that, then you get me."

"Alright." He brushes himself off. "How will I know when? I don't even know your name."

"Take a walk now and then. I'll find you."

With that, she pulls down the brim of her hat and steps away into the shadows. In moments, she's gone. He fastens his coat, and with one final look down the alley, turns and heads for home.

Posted Jun 4, 2019, 3:10 PM UTC

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