Triple Dog Dare

By Sensei

Original link:

Tags: dare, prostitution, severe, cane, paddle, strap, bondage

Added: 01 Jul 2012 Views: 12562 Avg Score: 4.67

(Y is for Yvette) Yvette finds out how far she'll go for the money
Yvette would have fidgeted, but her current circumstances made that impossible. She was naked, fastened securely, face-in, to a saltier cross. She looked over her shoulder nervously at John. That wasn't his real name, of course, but she had to call him something, and, though it was stereotypical, it worked for both of them. John had been a regular customer at Madame Decreaux's brothel for over a year, and he had long since picked Yvette out as his favorite. The establishment catered to a wide variety of desires, but Yvette spent much of her working day in the basement, which served as the dungeon playroom. John paid generously to have his way with Yvette. There was a safeword - unromantically, it was simply "safeword" - and there were security personnel on hand if any of the clients got unruly. That had happened to Yvette before, but never with John. Yvette, like all women in her line of work, was an accomplished actress in her own way. Still, she was good at her submissive role mostly because it was what she enjoyed. Some clients were mere dabblers in sadism. Their pitiful attempts at inflicting pain required her to employ her aforementioned acting talents, conjuring up tearful pleas for mercy. But John invariably brought his A game with him, and he established early on that he wanted honesty rather than playacting. When she cried for him, it was always real, and more often than not, he achieved it, making her pussy simmer as a side effect.

At the end of his last visit, he had remarked that, despite his best efforts, he had not yet wrung the safeword out of her.

She explained, "I've used it with other customers, but usually only with those I don't trust so much. I've known you so long, I doubt there's anything you could do that would make me use it."

"That's a pretty ballsy thing to say, Yvette. Even after all this time, you don't even know my name."

"Names don't matter. I know you pretty well, John."

"Well, I don't see why we don't put that little proposition to the test. I'll bet you your fee I can make you 'tap out.'"

She laughed and said "Now why in the world would I agree to that? I'd be inviting you to do something to me I hate and then not have to pay me? That's stupid."

"No, no, that's not what I mean. I want a fair challenge." He thought for a moment, then continued. "How about this: I'll tie you to that cross over there-" He pointed to the saltier cross as he said this, "and I'll only spank - only on your bottom. My choice of implement, but only what's in this room. And I get a half hour. If I can't make you stop me, I'll pay you double. Otherwise, the regular rate. Deal?"

Her eyes narrowed. She looked over at the rack of equipment on the far wall. It had a thoroughly complete assortment of paddles, whips, canes, tawses... She had, of course, experienced all of them by this point. She ran through the arsenal in her mind quickly trying to calculate whether she could endure a half hour of any of them on her ass. She was worried about the paddles. Surely a savaging from one of them would leave her black and blue for a week.

"Make it triple and you've got a deal. If I win, I'm probably going to need a couple of days off."

He smiled, "You can count on that, Yvette."


As she looked back from her vantage point at the end of the room, John reached into his pocket and pulled out a wad of currency. He waved it in the air and said, "Here's what we're playing for, Yvette. You outlast me, and it's yours." With that, he walked over to the bed at the opposite side of the room and placed it on top. He then walked over to the equipment rack and selected a round headed leather paddle. Yvette quickly did some mental calculus. That paddle was one of the less harsh implements. If he warmed her up with that, then she stood a much better chance of winning. He walked over to Yvette and stood close by her. He looked her in the face, "Here we are, Yvette. You know where the clock is-" he glanced over to the clock on the wall. Each room in the establishment, naturally, had a clock in it, given the rates were generally hourly. He continued, "It's coming up on 8:30. If you make it to 9:00, you win." He paused for a moment, "And here we go."

With that, he let go a full stroke on the full of her left ass cheek. She was, naturally, quite experienced, and the beginning of a spanking was never much of a surprise. But he clearly was not going easy on her. In spite of her self, she said, "Oh my God," out loud. He smiled and struck again in the exact same spot, bringing an "Ooowwww!" from her. He lashed out again on the same spot a third time, and she screwed her eyes shut and almost succeeded in suppressing a squeal. He paused for a moment, and then unleashed the same sequence of punishment on her opposite ass globe, giving it a matching shade of pink. Yvette tensed her body up with his assault, and when he paused, she relaxed and began to pant.

Yvette saw him reach into his pocket and pull something out, but she couldn't tell what it was. He gave her four quick spanks on each cheek, forcing her to tense up again. As he paused, he reached between her thighs and probed her pussy. It was wet and he chuckled at the discovery. Yvette heard a faint buzzing noise start and then felt the buzz on her clit. She shuddered. He was using a vibrator on her! Her brain was filled with a thousand conflicting voices. Distantly, she knew that he was trying to draw an orgasm out of her quickly... She thought about resisting, but the buzzing on her clit was impossible to ignore. She started to moan and pant. Without warning, the paddle impacted on her ass again and she cried out, momentarily distracted from the pleasurable sensations from her clit. The paddle struck again on the opposite cheek and drew another cry from her, but the insistent buzzing on her clit was urging her towards the inevitable. She started to alternate moans with her panting, and finally tensed up and cried out, "Oh God, yes!" After a moment, she began to relax and sighed deeply. John pulled the buzzing vibrator away from her pussy and grabbed a hank of her hair and twisted her face around to look at his. He stared into her eyes, which were glassy with the pleasurable afterglow, "Very good, Yvette. That only took 4 minutes. And with that out of the way, now the games can begin in earnest."

A pit opened up in her stomach, but she said nothing. He walked back over to the equipment rack and traded the leather paddle for a cane. He swished it in the air a couple of times, testing it. She was certain he did it to try and intimidate her. Ordinarily, it wouldn't, but today, the stakes were higher. She looked over at the clock. 25 minutes still to go. He walked back and took up a position two paces away from her and tapped the cane menacingly on her ass. She closed her eyes and steeled herself. The cane whistled through the air and painted a line of burning fire across the middle of her ass. He gave her no time to react to the first stroke but quickly gave her another, and then a third. She gave up on attempting to track them as the stinging fire built up in her ass, forcing her to cry out. He stopped and she started to cry, mixing her sobs with, "Oh my God!"

He let her calm down for a moment and then moved once again to her side, grabbing her hair to force her to look into his eyes, "You were just about to stop me, weren't you?"

She sniffled, but tried to sound defiant saying, "No," but her voice wavered.

"Liar. But that's alright. You see, Yvette, I know there's no way you could last for a half hour of that. But if you stop me, then I don't get my money's worth even if I get the extra cash back. No. I can't just break you quickly, my dear."

Her lip trembled. She knew he was trying to intimidate her, but she also knew it was working. She looked at the clock. 22 minutes to go. He saw her glance away, "Don't worry about the clock, Yvette. Worry about me."

He went back to the equipment rack and selected a long wooden paddle, coming back with both the cane and paddle. Yvette's eyes grew wide, and she said, "Oh, no."

"Oh, yes, my dear."

She whimpered, "Please."

"Don't beg, it's beneath you. You want me to stop, you just say the word - you know the one. Say that word and I'll take my money and go."

She heard the challenge in his voice and her mood darkened. She steeled herself and more confidently hissed out, "Never."

He smiled and took up his position a couple of paces away.

He put the cane under his left arm and took the paddle in his right hand and quickly gave her a full stroke across both ass cheeks. Her entire conscious mind was immediately and completely filled with the burning pain in her bottom. As her cry filled the room, it was joined by the swishing noise of the cane as it flew through the air and landed where the paddle had just been. She shrieked as the cane fell four more times in rapid succession. There was a pause and then the sound of the paddle's meaty splat filled the room again. He continued to alternate between the paddle and the cane while Yvette cried incoherently. He paused and dropped his tools and grabbed her by the hair again, "Say it!"

"No!" she sobbed some more, "No, I won't! You can't make me!"

Her eyes were red and angry, and her tears mixed with her mascara, leaving black tracks running down her cheeks. She coughed and sniffled, trying to regain her composure. Trying to be brave. She looked back at the clock. 15 minutes. He saw her glance away from him to the clock and he looked after her and smiled. "Only half done, Yvette. And you're barely hanging on now as it is. Is it worth it?" He raked her battered ass cheeks with his fingernails as he asked.

She cried out more in surprise at this new assault, and then hissed her response, "Yes! Yes! You can't break me!"

"We'll see." He let go of her hair and walked over to the bed and sat down. Yvette sniffled some more and then asked, "What are you doing?"

"Your ass is undoubtedly getting numb. I intend to let you recover just enough..." he let that thought hang in the air unfinished. Yvette gulped and relaxed while John pulled out his phone and started to play with it. She was sure he was only pretending to ignore her. She took the opportunity to move her wrists and legs as much as her restraints would allow, trying to work out the stiffness that tensing her muscles so repeatedly had brought on. She tried to look over her shoulder at her ass, but couldn't see it. She could certainly feel it, however, as it throbbed in unison with her heartbeat. It felt burning hot and she wanted nothing more in this world than to rub cooling lotion into it. Well, she corrected herself, almost nothing.

Finally, John stood up and went back over to the equipment rack. He selected a long, heavy razor strop. Yvette's jaw dropped. That strop was the very embodiment of evil. As he walked back to her, she shuddered. He saw her reaction and smiled.

"Oh yes, I know very well that you two are very well acquainted, Yvette. You can spare yourself, of course..."

She was unable to speak, but she shook her head. She looked back at the clock. 5 minutes to go.

"Everything that I've done so far has been just a warm-up, Yvette. Your ass is already bruised. I know you know that. I've left only 5 minutes on the clock, but I know damn well, there's no way I'll need all that time. I will say, Yvette, there's no one I have ever played with in all my years that has been able to go this far. And you know what I realize now? Even if I lose, I win. Because I've been able to go further with you tonight than I know I ever would have. Am I right?"

Yvette looked away from his eyes and nodded.

"I'd love to continue to talk, Yvette, but time's a-wasting."

He stepped back away and raised the strop and hurled it across the center of Yvette's ass. She screamed louder than could ever remember screaming before. He paused while she recovered, and then lashed out with the strop again. Again, she tensed all of the muscles in her body as one and her entire consciousness became nothing more than the primordial cry of animalistic pain she felt. He lashed out a third time and she continued to cry, but as she did, she felt herself drift away to the place where she became a spectator to her own ordeal. He continued to emblazon her ass with the strop's heavy impacts, but the impacts became more distant as she retreated into her mind. But as he continued, his savage punishment reached in after her. She couldn't hide herself from it any longer. She heard herself sob out "safeword!" her voice barely working properly enough to make coherent syllables.

She cried anew, cursing herself for her weakness, frustrated that she had endured so much for nothing. She kept her eyes closed as the tears flowed from her eyes. She had cried so much a part of her mind marveled she was still capable of it. She felt him release her legs from the restraints and help her stand. She wished he would just leave her staked to the cross forever. He released her arms and she almost collapsed at his feet, but he held her and helped her over to the bed, laying her down gently. She buried her head in her hands and sobbed.

He interrupted her crying by grasping her hand and wrapping it around the wad of money he had left on the bed earlier. He simply said, "Here."

She was dumbfounded. She looked up at him with a questioning look, "But... but I said 'safeword.' I lost."

He shook his head, "No. Time had just run out. You said it after my last stroke. You won."

She couldn't quite comprehend what he was saying for the longest time. She just looked at his face. Finally she looked back at the thick wad of cash and asked, "I did it?"

He smiled, "Yes, you did, Yvette. I tried every trick I know to break you, but you beat me."

She sniffled and smiled. And then she frowned and said, "I'm sorry."

He caressed the back of her head, "No, Yvette, don't be. This is a night I won't soon forget. You were worth every penny, I can assure you."

"No, I'm sorry, I can't see you anymore after this. You're never going to be able to be with me again without comparing it to tonight, and I can't.... I don't even know.... I'm not going to be able to work again until this heals."

He thought about that for a moment.

"What if you didn't have to work?"

She gave him a puzzled look.

"I mean, what if you didn't need the money? What if you were with someone who would take care of everything your money could buy? What if... you were mine?"

She looked into his eyes for a long time, pondering the question.

"Let me think about it."

He smiled and said, "Deal."