Roll of The Dice

Vanessa racked her brain, trying to remember Colleen. Then it clicked. They had met at a Female Leadership workshop; both were speakers and successful businesswomen navigating a man's world. They had shared a few drinks and conversations at the hotel, but that was the extent of their interaction. Why had Colleen "sponsored" her? Vanessa couldn't understand it.

Erin interrupted her thoughts. "Colleen thought you might become one of us, with a little guidance, of course. But I'm afraid you fucked that up for yourself." She leaned in closer, her voice a low, menacing whisper. "You'd better hope that Colleen wants to take her embarrassment out on you."

Erin released the speech constraint on the collar. Vanessa, her voice hoarse, provided the managers' names and the necessary details. The texts were sent, and Erin quickly turned the collar back to silent mode. She grabbed the scissors she had used to shear Vanessa's hair and clipped the zip ties securing Vanessa's ankles to the chair. Vanessa groaned in relief as she finally managed to place her feet on the floor.

Next, Erin released the rope that had been forcing Vanessa to bend, but she left it hanging from the collar. Finally, Erin unlatched the ratchet on the cargo strap that had been holding Vanessa to the chair. Vanessa groaned again, stretching her body as best she could with her arms still trapped behind her. Her skin was marked with angry red lines from the heavy webbing, and her ankles showed deep, raw sores where the zip ties had cut into her flesh.

The room was filled with a tense, charged silence as Erin moved in close, her gloved hand slipping between Vanessa's legs. She stroked the naked bush, her leather-clad fingers parting Vanessa's lips and delving inside. One, then two, and finally three fingers, all moving independently, explored her depths. There was a fleeting moment of pleasure, quickly replaced by pain as Erin pushed in hard, almost lifting Vanessa off the floor. She repeated this brutal intrusion three more times, bringing tears to Vanessa's eyes.

Erin pulled back her fingers, took a deep, contented sniff of her gloves, and then offered them to Vanessa. Without hesitation, Vanessa licked and sucked each one clean, her tongue working carefully.

Erin then reached for her crop, a slim, wicked-looking implement. She moved all the chairs to the side of the room, clearing a path so she could circle Vanessa completely. She did just that, her touches light and teasing at first, making Vanessa jump and flinch. Then, without warning, the first slash came down hard on Vanessa's backside. Vanessa jumped and screamed, the collar around her neck coming to life, delivering a sharp, burning shock. "I'd be quiet if I were you," Erin warned, her voice cold as she brought another blow down on Vanessa's stinging bottom.

Blow after blow rained down on Vanessa's body, the crop biting into her legs, arms, stomach, and thighs. She yelled out in pain, earning two more shocks from the collar, each one searing her neck like a brand. Erin watched, a twisted smile playing on her lips, secretly impressed by Vanessa's restraint. She had expected more screaming, more pleading, but Vanessa's cries were surprisingly controlled.

Vanessa was a mess of tears and sobs, her body a roadmap of red, raised welts. She didn't have time to catch her breath before Erin grabbed the rope and pulled her roughly toward the doorway. "Come on, slut," Erin commanded, her voice laced with anticipation. "There's a nice big cock upstairs, and my pussy wants to find out if it feels as good as it looks.”

On their way up to Vanessa's bedroom, where Jack was hooded and secured to the bed, Erin made a quick stop in the bathroom. She took her time, relieving herself with a satisfied sigh. Then, she sat Vanessa down and told her to do the same. To Vanessa's surprise, her bladder cooperated, and the pee flowed out easily.

As Erin told her to stand, Vanessa suddenly retched, a deep, convulsive heave that turned her face a sickly white. Erin had expected this reaction after forcing her to eat the cigarette butts. She grabbed Vanessa by the shoulders, turned her toward the bathtub, and shoved her gloved hand into Vanessa's mouth, tickling the back of her throat. In a flash, she withdrew her hand, and Vanessa vomited a vile mixture of cigarette ash, butts, and partially digested food, all splattered along the bottom of the tub.

Erin counted three butts among the mess, deciding that should be enough. She held Vanessa there for a few minutes, ensuring nothing else came up. Finally, she washed Vanessa's face off over the sink, her touch surprisingly gentle despite the circumstances.

Vanessa was shaking, her body wracked with shivers as Erin dragged her into her own bedroom. There, secured to the bed, was Jack, still hooded, but his once-erect cock now lay flaccid and limp along his stomach. Erin pushed Vanessa forward roughly, grabbing the back of her neck and forcing her head down until her mouth was level with Jack's cock. "Get that hard for me," Erin commanded, her voice leaving no room for argument.

Despite having just been sick, Vanessa knew better than to disobey. She started with Jack's balls, hairless and smooth, remembering she had shaven them just the day before. She sucked each one gently, her mouth working diligently. Then, she ran her mouth up the soft length of his cock, tickling the tip with her tongue. She felt a spark of satisfaction when she saw it twitch, a sign that her efforts were having the desired effect.

Vanessa's efforts paid off as she managed to take the end of Jack's cock into her mouth, her tongue working in tandem with the sucking motion. She moved her head up and down, her skill evident as Jack's cock quickly grew hard and pulsating. When Erin noticed, she roughly pushed Vanessa aside. Jack's cock popped out of Vanessa's mouth with a wet plop, standing straight up, ready and waiting.

Erin shoved Vanessa to the floor and stepped over her to climb onto the bed. She straddled Jack, her hands wrapping around his cock as she positioned herself. She gave it a tentative stroke before slowly impaling herself on it, a loud sigh of pleasure escaping her lips. "It isn't as big as my husband's," she thought, "but it's more than adequate."

She placed her hands on his chest and pushed down, her body responding to the sensation. She rode him with purpose, knowing the silicone ring she had placed around his cock earlier would delay his orgasm, but not prevent it entirely. To heighten the experience, she reached up and twisted the disc on his hood, cutting off his air supply. Jack began to panic, his body bucking as he desperately tried to find air.

Erin cried out in pleasure, the feeling of her power combined with Jack's struggling body pushing her over the edge. She climaxed with a scream, her body convulsing with release. Only then did she lean forward and turn the disc back, giving Jack a chance to breathe again, his chest heaving with each ragged gasp.

She remained still for a moment, fully impaled by Jack's cock, her pussy throbbing around him. She savored the sensation, her body humming with satisfaction. Then, she began to move, slowly at first, teasing both herself and Jack with deliberate, torturously slow strokes. She leaned down, her teeth finding his nipples, biting and sucking until they were red and marked. Her mouth traveled lower, leaving a trail of teeth marks and hickeys on his chest as she worked him hard, his body straining against the restraints.

She could feel him growing, building towards his own climax, his cock pulsing in time with her movements. Her own pleasure was building again, the friction and the power she held over him pushing her closer to the edge. With a final, intense orgasm, her body convulsed around him, and almost immediately, Jack exploded inside her, sending waves of pleasure crashing through her already sensitive, sore pussy. She cried out, her voice a mix of pleasure and triumph, as she rode out the aftershocks of their shared release.

Erin slid off Jack's softening cock and stepped down from the bed, positioning herself right over Vanessa's head. "Clean me, bitch," she shouted, her voice firm and commanding.

Vanessa shuffled around on her knees until she was directly beneath Erin's dripping pussy. Erin sighed in satisfaction as she felt a tongue lick her, followed by soft lips pressing against her sore, sensitive flesh. Vanessa worked diligently, her tongue and lips cleaning every trace of Jack from Erin's body. When Erin was finally satisfied, she stood up, leaving Vanessa and Jack behind as she made her way back downstairs.

She found her clothes and dressed quietly, taking her time to make sure every button was fastened and every zipper pulled up. She sat in a chair, relaxing with a well-deserved cigarette, the smoke curling around her as she exhaled slowly. When she finished, she reached into her bag and pulled out one more item: a rubber hood, identical to the one Jack was wearing.

Erin made her way back upstairs, her footsteps quiet on the carpet. "Up," she ordered Vanessa, her voice leaving no room for argument. Vanessa struggled to her feet, her arms still strapped behind her back, but she managed to stand upright without Erin's help.

As she stood, Vanessa caught a glimpse of herself in the dressing table mirror. She looked dirty and tear-stained, her hair cut unevenly, as close to the scalp as Erin could manage. Her body was covered with slash marks from the crop, a map of her ordeal.

Erin grabbed the rope and pulled Vanessa toward one of the bedposts. She wrapped the rope around the post two or three times, tying it off securely and leaving Vanessa trapped against the bedpost, her face turned away from the room.

Erin picked up the hood and, without hesitation, slipped it over Vanessa's head. She positioned it carefully, pulling the straps at the bottom to secure the mask in place. She turned the disc on the front, watching with a twisted sense of satisfaction as panic appeared, Vanessa struggling desperately for air. Only when she was sure that Vanessa was fully submerged in her terror did Erin turn the disc back, allowing her to breathe again.

Satisfied with her handiwork, Erin left the room and headed downstairs to make the call. "Pick up both of them," she said into the phone. "They are in the main bedroom. Could you also send a clean-up crew? Thank you." She pocketed her phone, grabbed her holdall, turned off the lights, and left the house, leaving Vanessa and Jack to their uncertain fate