The Wager

He places his neat stack of fifties in the safe. Always appreciative of a nice visual, she brought her bet money in various denominations for a slightly larger pile, though equal in value.

"Are you expecting me to celebrate my win at the strip club?" he teases.

"I want you to fuck me on a pile of my winnings," she corrects. They both know bragging rights are the true prize though.

He turns around while she sets the four digit combination. She places a timer on top of the safe. Her hand hovers over the button as she takes a deep breath.

"Time starts in three, two, one."

When he turns back around to face her, the warm, flirty smile is replaced with a mischievous grin. His eyes sparkle with sadistic anticipation like they do when she's earned a punishment.

"Strip then face down on the bed." She slowly lifts her shirt up over her head. "Don't waste time. Quickly," he growls, eyeing her like prey.

Once naked, she lays on the bed on her stomach. He swats her behind. "Ass up, on your knees. I bought something new for tonight." He coaxes her legs wider before securing each ankle to a spreader bar. Her pussy is fully on display and oh so vulnerable. She shivers.

"You're already so wet." He trails two fingers through her damp folds. "So when do I start asking for the combination?"

"Whenever you want, but I'm not going to give it to you." He responds to her sass by plunging his fingers into her mouth until she licks them clean, effectively hushing her for now. He fastens her wrists to the bar outside her ankles, forcing her chest into the bed and locking her immobile.

The first victim of the crop is the bottom of her left foot with little pitter-patter taps and ticklish strokes. He can't resist her bare, upturned feet and he's playing to win. He knows this is her least favorite place to be touched.

The strike squarely on her ass makes her flinch. He varies the location, the intensity, and the speed of his strikes, making it excruciatingly impossible to anticipate his next move. Pink marks bloom beautifully on her fair skin.

The leather makes wet slapping noises against her increasingly-sensitive pussy when he focuses his attention there, beating a rapid rhythm until she mewls softly.

"Just give me the first number of the combination and I'll switch to something else."

"No," she groans.

"Think about it. The cane is up next." He sits on the bed next to her, but she can't see what he's strapping to her thigh.

She jolts when the wand starts buzzing. He's positioned it with enough pressure to drive her crazy, but not enough to make her cum. She squirms just to be sure release isn't possible.

"Still a no?" he asks before leaning in to crudely spit on her puckered hole. His breath tickles as he asks if she's sure.

She doesn't respond as he teases her ass, rubbing little circles over her entrance then slowly pushing a finger fully inside before withdrawing. Again. And again. She stifles a frustrated moan. He inserts two fingers, twisting and spreading them to stretch her.

She had envisioned giving up the combination to the safe to save herself from torture, not to earn an orgasm. She breathes deeply, trying to focus on anything but her growing arousal and the vibrations against her aching pussy.

He removes his fingers and she strains her ears for any indication of what's coming next. Lube. She hears the squelch of the bottle then feels something cool against her ass. It's not her cute pink plug. This intrusion is harder, more bulbous. It meets more resistance.

The cold steel fills her, opens her further than any of her other toys, but it's still not seated. She shifts her weight, but he doesn't let up his firm, slow pressure until she takes it all. It's so heavy, keeping her fully aware of it's presence while he leaves her on the bed.

He doesn't ease into the caning like he often does. The first thwack makes her yelp.

"You've been such a good girl so far." He attempts to soften her with praise between strokes. "Just give me the first number... I'll put away the cane and I'll let you cum."

He punctuates his offer with quick successive strikes on her already-tender ass. It's only one number and surely significant time has passed. "Six."

"That wasn't so hard, was it?" He unstraps the wand and presses it to her clit. She whimpers from the intensity, but feels herself climbing fast. He'll keep his promise, but he won't waste time.

An orgasm rips through her. Her binds prevent her from arching her back or stretching her muscles, which threaten to cramp. He holds the wand firmly against her throbbing pussy.

"Again," he demands. She can't pull away, can't escape the overwhelming vibrations. Her body shudders again, but he doesn't let up.

"Again."

The threshold between pleasure and discomfort is approaching rapidly. The vibrations consume her. Even her fingertips seem to buzz. Her core clenches and the muscles of her pussy contract weakly.

"Again." She shakes her head, whining in protest. "Again," he growls, grinding the wand against her tender clit. "Or give me the second number."

She cries out when he robs her of another orgasm. Her limbs feel wobbly. She rolls her hips away from him, but that only makes him chuckle at her feeble attempt to escape. He's not going to remove the wand until she surrenders more of the combination.

He spanks her hard. "Is it a one?"

His bare hand on her tender flesh only increases her arousal. "A two?"

"Three?" She can't take another second of the wand or another orgasm in this position.

"Four?"

"Yes."

He turns off the wand. "What was that?"

"It's four. Six, four," she sighs.

"Good girl." He releases her from the spreader bar and she collapses on the bed. The heavy plug still presses against her insides, but at least the wand has stopped. The room is so quiet without the buzzing.

She rolls over to watch when she hears him removing his pants. He tosses a bag on the bed. When she sits up to peek inside, he grabs her by the hair and pulls her back down, dragging her head off the edge of the bed. She smiles up at him, feeling confident about how much time has already passed and knowing she'll enjoy his next attempt at extracting information. Her tongue dances on her lower lip in anticipation.

He shoves his cock down her throat until she gags. She places her hands on his outer thighs, but doesn't push him away. He stays buried in her mouth as he leans forward to roughly mold her breasts. His fingers pinch and twist her nipples until she moans around his cock.

He withdraws to remove nipple clamps, a flogger, and a ring gag from his bag. It's his turn to smile when he sees her reluctance towards the gag. That's exactly what he starts with, forcing her mouth wide.

"All you have to do is say a number and all this goes back in the bag."

The stubbornness and determination in her eyes as she shakes her head makes his cock twitch. He prods her open mouth with a finger. The drool is already starting. He wipes it on her face before fastening the clamps.

The long chain of the clamps in one hand and a flogger in the other, he stands over her, ready to claim his third battle of the evening. She can still win though if the timer runs out. He drags the tails of his chosen tool over her chest then caresses her face before positioning his cock just barely outside her lips, close enough to feel her breath.

"Ask for it." Her only response is to frown, so he pulls the chain taught then repeats himself.

She mumbles something intelligible. "Good enough," he approves as he thrusts his hips forward, threading the gag. Her body convulses as she chokes on him. The tug of the clamps makes her arch off the bed, but he only pulls higher.

The flogger swishes across her stretched breasts relentlessly. She cannot see the timer, hasn't seen it since starting it, but she senses he's behind schedule. He alternates between teasing her with the flogger and frantic sessions that make her grit her teeth. As she squirms, the base of the plug presses against the bed.

He drops the chain and pauses his assault with the flogger to focus on fucking her face. The image of her writhing on the bed is too much. He needs to cum.

He pulls out to spill his load on her face and into her forced-open mouth. She looks up at him with watery eyes from the hard fucking. Tears, drool, and cum coat her flushed face.

Chain back in hand, "I'll take that third number now."

She shakes her head and he pulls harder. Her upper body lifts off the bed.

"Don't make me ask again." One clamp slides off and she yelps.

"Nine."

"Good girl." He releases the other clamp gently, the sensation now returning to both nipples, leaving them aching and tender. He rolls them between his fingertips then removes the gag.

He has three of the four digits to the combination now, but time is expiring quickly. She's worn down, but clearly still determined not to give up the full combination.

As they assess each other, she smiles, her eyes twinkling with challenge.