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When the Dark Wins by Addison Cain, Jennifer Bene, Cari Silverwood, Zoe Blake, Yolanda Olson, Dani René, Eris Adderly, Michelle Brown (13)

11

Anthony watched as she pressed herself forward against the cool, concrete wall. Wrists in dark cuffs, arms spread wide, linked to the hard points high above her head. He had always enjoyed this design. The chains allowed him to adjust based on their height so he could make them stretch. Even now, she was up on her toes, calves shaking from the strain, round ass catching the harsh overhead lights.

It had been two weeks of things like this. Creative punishments, mind games, but the girl seemed more defiant than ever.

She’d even told him to kill her.

So ridiculous.

First, slaves were not allowed to make demands.

Second, he didn’t believe for an instant the girl truly wanted to die. No living thing did. It was hard-wired into their biology to survive — and no matter what he did to her, she would always crave another breath.

Most importantly, this was a business, and good businessmen never invested time and money in something only to abandon it at the first hint of hardship.

He just needed to be rougher with her. Make her suffer more.

Running the leather of the whip over his palm he focused on the handful of bright red lines across her upper back and shoulders. “What are you, girl?”

Her body jerked, twisted a little as she shifted her weight between her feet, but she didn’t answer. Fingers wrapped tight around the chains, she was either extraordinarily strong, or impressively stupid.

“Silence is defiance. Do you need another reminder?” Uncoiling the whip, he let it hang to the floor once more. Waiting, watching as he adjusted his grip and moved to the side again, letting her hear his footsteps — but she still didn’t speak.

Lifting his arm, he swung forward, hearing the whip snap against her flesh a second before a guttural cry left her lips, soft whimpers following. Another bright red line formed, and he wondered if she knew he could strike so much harder. Could make those lines purple, could make her bleed.

“What are you, girl?” he repeated, and it irked him. He’d asked the same question so many times and he despised repeating himself. A waste of time and energy. “Answer me.”

No,” she whispered between harsh breaths, her jaw muscles twitching as she pressed her teeth together again.

Another crack of the whip, harder, and she gasped before she screamed. This line was going to be darker, a lovely reddish-purple. It probably hurt, a lot, but he had never been whipped so he didn’t know exactly what it felt like.

“FUCK YOU!” the girl screamed, voice breaking at the end of the expletive as she dissolved into whines, rattling the chains with her twists and tugs. It was a pretty sight from the side. Round breasts brushing the concrete, flat stomach twisting above wiggling hips.

The customers are absolutely enjoying this.

Walking over to the table he set the whip down and picked up the bar gag. She was still breathing harshly when he approached, refusing to look at him as she leaned her forehead against the wall. There was no doubt in his mind that it was her exhaustion, and not some last minute attempt at obedience that kept her eyes averted.

She was disobedient to the core, but he had something else after the whipping to break her a little further.

“Open your mouth.” That drew her attention, head twisting to look over her shoulder at him, and he lifted the gag so she could see it. Brown eyes went wide, and her jaw tightened.

Anthony was somewhat fascinated by her. Normally, there was so much pleading and begging, especially when he used the whip — a boorish, yet painful implement if there ever was one — but she was still cursing. Still brazenly refusing to submit, and nowhere near breaking.

Weaving his fingers into her hair he ripped her head back, the natural gasp of breath into her lungs opening her jaw, and he shoved the leather bit between her teeth before she could correct it. It only took a moment to wind the leather behind her head, under the ponytail he had roughly pulled together to keep it off her back.

She sputtered curses around it, still loud, but less intelligible.

Much better.

“I did tell you what would happen if you cursed at me again, remember, slut?” He stroked her hair, smiling when she pulled away from him. “Ready for the rest of your whipping?”

A garbled stream came from her, and he could almost pick out the obscenities as he returned to the whip. The leather was still warm from his hand, a comfortable hold.

“If you would like to answer my questions from this morning, or address me properly, simply snap your fingers. Otherwise, we will finish this part of your punishment.” Anthony watched as the muscles in her back twitched, her legs bending and straightening. Preparing for the pain.

It wouldn’t help her, of course, but he allowed her the moment anyway.

Sometimes, he was too generous.

Rearing his arm back he snapped the whip across her shoulders, reveling in the scream as his cock twitched. Still sated from before he’d chained her up, but he enjoyed it anyway. Another lash, harder, and her back bowed before she pressed her body into the concrete.

Darker.

That line was already a deep purple, and he listened to her sob, the slurping sounds around the gag as she tried to avoid drooling.

In a moment none of that would matter to her.

The whip arced through the air so fast his eyes couldn’t track it, trusting his skill to land it where he wanted, and over and over it did. Practice makes perfect, or so they say, and though he’d prefer the marks to be more evenly spaced, they were still grouped carefully across the top of her back.

Eyes roving to her ass and thighs he admired the clean expanse of flesh, the belt marks having faded from his brother’s interlude with her, and he smiled. Shifting his feet, he angled lower and the whip cracked at a diagonal across her ass.

A new scream, guttural sobbing. She hadn’t expected him to strike somewhere new.

Anthony paused a moment to enjoy her despair, the hiss of her breaths around the gag, the whimpers, the occasional sucking in as she fought to swallow the saliva he knew was pooling in her mouth. He could have put her in a ball gag, but that was for shorter durations than he planned to have her in this one.

Tonight, he would torture her in new ways.

But first, the whipping. Two more lashes across her ass, dark ones that drew out the most desperate screams of pain, and then he added another across her shoulders. The girl bucked, crying, and he saw the first string of drool spill from her lips. It glinted in the light as it spilled onto her breasts, and she whined, sputtering as she gave in and let more flow.

How many emails had he received requesting a whipping?

Too many to count at the moment, but he looked forward to reviewing the live cam views on this session. It had lasted long enough that some of the customers would have reached out to others they knew, encouraged them to access it.

Which meant she needed to perform.

“Want to snap your fingers, slave?” He taunted, moving forward to run his hand across the welts on her ass, squeezing hard to turn her soft whimpering into another pain-filled scream. Leaning closer he spoke almost directly into her ear, “If you do it, I might even stop. Isn’t that what you want?”

She jerked violently against the cuffs, anger suffusing her incoherent shouts, he even thought he heard a garbled fuck you in the mess — but she didn’t snap her fingers.

It was like she knew what he really wanted in that moment. As perfunctory as it would be for her to break now, to submit, it would be so disappointing. He wanted to hurt her more, wanted her to scream more, wanted to break her down into component parts until he could reassemble her into something marketable.

Which, at this rate, would take so much time.

And he planned to appreciate each and every moment of her destruction.

Moving to the opposite side of her, he rolled the handle of the whip in his fingers, and then gripped it. His muscles twitched in anticipation, cock hardening again as he caught the sheen of his come on her thighs. She was already a slave, already a thing, she just hadn’t accepted it yet.

The next whip strike across her ass crisscrossed a previous one and she wailed, one foot lifting off the floor like she could block the pain, and then he struck her upper back. She arched, head angled back as she sobbed, and he wondered what she was feeling.

Was there fear in that complex soup of anger and pain? Did she know he could draw blood with the whip? Was she waiting for it?

A visual of crimson streaks rolling down her back filled his mind, and for a moment he even felt tempted. It would just take a little more strength behind the whip to cut flesh like butter. He could tear her to ribbons and listen to her weak screams until she blacked out. Something about the idea was tempting, despite the inherent mess of the blood and the inevitable risk of infection and scarring.

No.

Damaging the merchandise was foolish, and he was never foolish. That was Marcus’ territory. Impulsive and imprudent. Eventually she would need to make him money, and while the whip marks were getting darker, they would heal without lasting scars.

He had waited too long between strikes with his internal musing. Her breaths were evening out, she wasn’t even sobbing anymore despite the occasional sniffle.

If he couldn’t make her bleed, he’d just make her suffer.

Lifting his arm he brought the whip down hard over her upper back, then her ass. Back, ass, ass, back, again and again, and then just as she was screaming herself hoarse he landed the whip high on her thighs. The girl’s legs gave out as she sobbed weakly, hanging by her wrists from the cuffs — an added pain of her own making, but he didn’t want her breaking something.

Walking forward he wrapped the whip around her throat and used it to pull her back up, aided by his grip around her waist. She choked, coughed, sputtered against the gag as he tightened the whip, and his cock strained at his zipper.

“Do you want to submit yet?” he asked, watching her hands for any hint of an attempted snap.

Nothing.

He hadn’t planned to fuck her again, but there was nothing like screaming, or the desperate choking sounds coming out of her now, to make him hard. With her life in his hands, she was as pliable as she needed to be, too weak to stand on her own… but she wasn’t even trying to snap her fingers, and he had been so patient. Given her so many chances.

Anthony had refused to fuck her ass so soon after Marcus’ hasty actions, wanting to wait until the right moment, and now felt perfect. Dropping the whip he held on to her waist with one hand and unlinked one of the cuffs with the other. Her sudden intake of breath spoke of the hope she felt, the hope that the punishment was over, but he only moved the connector farther down the chain and then locked the cuff in place again.

She sobbed, the jerk of her body against his a clear indication that this was the right decision. The right moment.

With the second cuff shifted down he was able to pull her away from the wall, bend her forward, and she braced her palms on it, garbling pleas through the gag. He could hear a broken ‘please’, the barely perceptible versions of ‘no’ and ‘don’t’, but her refusals only made him smile because none of them were the answers to his questions.

The girl had not admitted she was a slave, had not called him Master, had not submitted.

“You understand what this means, girl. More punishment.” Keeping one arm around her waist, he opened his belt, his pants and zipper, pushing them down as he forced her legs wider. It strained her arms, forced her shoulders to twist, but none of that mattered as he freed his cock and slid into her hot cunt, still wet with the mix of the two of them. She hadn’t come, but he had, and her body’s defenses had made her more than wet enough.

Another contribution of his training.

Tightening around him, squeezing, she whimpered as his pants scraped over the whip marks. He moved inside her slowly, letting her believe for a moment that this was all he wanted from her. The girl started to relax, and he knew she was separating from this like she had so many times before.

It would be a short-lived reprieve.

He thrust a few more times, lubricating, before he pulled out and moved his cock to her ass. Body contorting, she whined as she tried to pull away, but his arm around her waist stopped it. She was so weak compared to him, helpless even without the cuffs. He could have done this a hundred times over, could have done it without wetting his cock inside her, but with her gagged and still crying from the pain of the whip?

This was the moment to take her ass.

“Have you realized yet that there’s nothing you can do to stop me?” he asked, watching her ribs expand and contract as she stayed silent. Defiant.

She was practically begging to be punished.

Unlike his brother, he slowly pressed against her tight ring of muscles. Waited for her keening whine to rise, for her body to shudder, her panic to peak, before he twitched his hips and forced the head of his cock inside her. So tight.

“I can do anything I want with you, because I’m your Master, whether you say the word or not. And when I sell you, it will be the same.” Her sobs grew louder as he moved deeper, inch by inch, stretching her as she fought and twisted. A strand of drool escaped her mouth, shining as it trailed towards the floor, and then he forced the rest of his cock in.

A scream escaped her, ending in a choked sob as she sputtered pleas, making the chains rattle when she moved her hands. Only the second cock she’d taken in her ass, it would still hurt plenty, and he was going to make her feel every bit of this violation. His brother may have been first, but he had rushed it — like he did everything — and so it would be this she remembered the most.

“You are not a person anymore, you’re a slave. Property.” Easing back, he thrust in a little harder, a little faster, ignoring the urge to tear her apart, focusing on every shiver, every whimper, every crumbling bit of hope.

But as much as she said she wanted to die, she would survive. He would make sure of that.

“You are nothing more than a body for men to seek their pleasure in, to torment for their entertainment.” Reaching forward, he caught her ponytail in his fist and wound it around to lift her head and pull her back on his cock, stretching her further. She choked out a pain-filled cry, eyes clenched tight as her fingers bent against the concrete. The sight of the gag between her lips, her tear-streaked cheeks, and the dark whip marks across her shoulders was perfect.

The customers will watch this over and over.

“I will take everything from you,” his voice was strained because she squeezed his cock inside her. Rhythmic, twitching pulses in the tight sheath of her ass, but he was determined to make this last. To make her suffer more than she had with Marcus, to get her one step closer to breaking.

“It’s up to you how long this lasts, slave.” He fucked her a little harder, enjoying the throaty groan that slipped around the gag. “You choose when the training ends. So, how much can you take before you snap?”

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