Sucker Bet

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Mistress Jane learns the hard way not to bet on a sure thing
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"One of these days in your travels, a guy is going to come to you and show you a nice, brand new deck of cards on which the seal has not yet been broken. This man is going to offer to bet you that he can make the jack of spades jump out of that deck and piss in your ear. Now son, you do not take this bet, for as sure as you stand there, you are going to wind up with an earful of piss."

From Sky Masterson's speech about his father's advice - from "Guys and Dolls." [The wording is as originally written by Damon Runyon in his short story on which the play was based. For the play, "piss" was changed to "squirt cider." and the speech became known as "the earful of cider speech."]

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* * * * * * * * * * * *

David Williams was known for two things, his absolutely over the top BDSM parties, and making– and winning– bets on almost anything.

His skill, or luck, when it came to betting was phenomenal. An example of his almost unbelievable luck occurred last winter when he was at a sports bar watching his favorite basketball team with several of his friends. It was a playoff game and his team was down four points with just seconds to go. Suddenly he offered, "Two hundred says that they still win. Who'll give me five to one odds on that?"

Jim Stout looked at him over his drink and replied, "I'll take your money."

No sooner had he said that than a forward launched a three-quarter court Hail Mary shot that swished through the net just before the buzzer. Also just before the buzzer was the shrill whistle of a ref calling a defensive foul on the shot, and then another whistle as another referee called a second foul on the defensive player for pushing the forward into the stands.

The clock was gone, so only the forward went to the free throw line. He had one for the foul on his shot and two for the following flagrant foul. If he made all three, they won. If he missed any of them, they lost. His free throw average was well under 200. Dave turned to Jim and asked, "Want to go double or nothing?"

Jim laughed and answered, "If you want to give me another hundred, I'll take it."

But the forward did something he had never done before... something unheard of. He shot underhand with both arms like a grade schooler on the playground. He made all three shots, and Master David's favorite team won by one point.

As Jim handed two thousand dollars to Dave he said, "You are the luckiest son of a bitch alive on the planet. ... That, or you can see into the future."

David just smiled at him and said, "Either way, you lose."

Luck like that was what made David Williams' bets legendary, but sometimes it wasn't luck. Sometimes it was a setup from the very beginning. David Williams was also legendary for getting people to accept sucker bets.

He knew every "bar bet" ever devised and had come up with several on his own. What makes a bet a "bar bet" is that often alcohol is involved in the impaired thinking process which causes a person to accept such a bet even knowing that it is most likely a setup that cannot be won.

What makes a bet a sucker bet is not the fact that it cannot be won or that someone was drunk when they accepted the bet. Then it would just be a bar bet. A sucker bet is a sucker bet because it is carefully set up in such a fashion so as to make some sucker think that they can actually win it. A sucker bet only works if the target truly believes they can win.

Most truly great sucker bets takes days, if not weeks or months of preparation so that everything is properly in place. But at last month's BDSM party, Dave proposed, on the spur of the moment, what was possibly his ultimate sucker bet.

Shortly after arriving at the party, Mistress Jane Henderson launched into a long tirade of derogatory remarks about those Master's who "waste so much rope just to restrain a submissive."

Dave took it personally since it was obvious that the submissive slave she was referring to was one of his. And he, himself, had tied her to the large oak tree at the edge of the patio.

David has his petite slave, vanessa, stand naked with her back to the tree and then swathed her-- and the tree, in soft, thick, black rope from head to foot so that she looked like a huge caterpillar in a giant black cocoon. The only things showing were her eyes which peeked out through an intentional gap in the rope and her nipples which were allowed to poke through between the layers.

Dave had intended it to be erotically artistic, and most of his guests agreed with him. Mistress Jane obviously did not. "I assume you think you could do much better," he said somewhat testily.

"I know I could do much better," she replied, "and I'm willing to put my money where my mouth is. I will bet you five thousand dollars that I can tie up a naked slave so she couldn't get possibly get loose with just three pieces of rope, each only two feet long."

This was a well-known bar bet among devotees of rope and Dave knew exactly the tie she was referring to. One rope is tied around the knees, one tied around the elbows and the third tied in back between the other two ropes pulling them into a tight hogtie. The result makes escape almost impossible.

The party guests gathered around silently as Dave seemed to consider her offer for several minutes. Then he made a counter offer. "Let's bet something that means something," he said, raising his drink to her in a mock salute.

"Money is, after all, just... money. I propose we bet ourselves." He smiled at her and took a sip of his drink before continuing. "The bet is this. Since you think I wasted so much rope artfully tying vanessa to the tree, I will bet that I can tie YOU naked to that same tree using just one piece of rope, one sex toy, and one leather belt. And you will have twelve hours in which to try to get free."

Mistress Jane looked like she was thinking about it. "I promise you," he continued, "that your body will not touch the tree; the rope will not loop around your body in any way; your hands and legs will be totally free; and you will still be unable to escape."

Such extra detail as to how the action of the bet is impossible is one of the marks of a bar bet, or in this case, a sucker bet. Almost anyone else would have walked away at this point, but Jane continued to look at him as if she was actually considering his wager. Then she spoke. "All you have to do is put the belt around my waist, tie the rope to the belt, and hoist me to the top of the tree. I wouldn't be able to get free because I would fall."

"Not what I was thinking," Dave replied. "But OK, I promise you, that your body will not touch the tree; the rope will not loop around your body in any way; your hands; and legs will be totally free; I will not pull your feet completely off the ground, and the rope will not be looped around the belt. With those conditions, I will tie you to that tree using only one piece of rope, one belt, and one sex toy of my choosing. And you will not be able to get free within twelve hours."

He laughed, lifted his glass once again in salute to her, and added, "And, of course, you will be naked."

Jane's face was again reflecting her thinking as she considered his wager.

"I won't make you get naked in front of everyone," he continued. "On the morning of my next party, you show up here before 8:00 am. It will just be the two of us. At 8:00 o'clock I will tie you to the tree naked. If you get free before the first guests arrive at 8:00 pm, I will be the one who will be naked when they arrive and I will be your naked slave for the duration of the party."

He smiled at her, "I think you would enjoy that."

He paused to let her picture that possibility in her mind, then he continued, "If you are still tied to the tree when the guests arrive, however, you are my naked slave until morning." He took a sip of his drink and looked out at his guests before adding, "I know I would enjoy that."

The guests could tell that Jane was now seriously considering the bet. What was prompting her to accept was that she was absolutely positive that she could escape. Dave obviously didn't know that she worked her way through college as a magician's assistant. Part of their act involved her escaping from what seemed to be impossible bondage proposed or executed by members of the audience. She smiled as she remembered the three summers in which no fair-goer at any of the county or state fairs had been able to tie her so that she could not escape in the twenty minutes allowed. And Dave was proposing twelve hours!

She knew that she would take the bet. She couldn't loose. But she remained silent hoping to entice Master David into proposing something further.

"OK," he began after a few minutes. "I'll sweeten the bet and give you an out if things don't go as planned. If you are not free at 8:00 pm, I'll give you a second chance... a safety bet, if you want to take it at that time. If you can get free by midnight– an additional four hours, then you are free from the bet. But if you are still bound when the last stroke of midnight rings from the clock in the tower of my mansion, you are my slave until the next party."

Jane smiled at him and bit her lip. She was still thinking.

He continued, "And you can ask any of the guests for help in figuring out how to get out of the bondage. They can't physically help you, but if you haven't figured it out, maybe they can give you some insight. You can back out of the bet all the way up to the time I start tying you to the tree, and you don't even have to consider that second bet unless you can't get free in the first twelve hours."

Jane finally said something, "Why not start out with the time period being until the next party. I could have a lot of fun with you in a month."

There was a gasp of appreciation from the gathered guests. Dave answered in one word, "Done."

"When would I have to tell you if I accept this bet of yours?" Jane asked.

"If you show up here the morning of the party," Dave replied, "you've accepted the bet. If not, I will see you at the party." He laughed. "Actually, I guess either way I will see you at the party."

Jane looked around at the Masters and Mistresses gathered around them. She said, "You are all witnesses to the terms of this bet. I am calling upon you to make sure that he doesn't cheat in any way. One rope, one sex toy, one belt; No binding of my arms or legs; No rope looped around my body in any way; my feet stay on the ground; the rope can't loop around the belt, and I can't be touching the tree."

She stopped and turned back to David. "Just to be sure. Which tree?"

He pointed to the large tree at the edge of the patio where vanessa was still cocooned in black rope. "That's the tree I've been talking about," he said. "It should do nicely. Do we have a bet?"

"OK," she answered. "You tie me naked to that tree at 8:00 o'clock on the morning of your next party. If I am still there at 8:00 at night– which I doubt, then I am your slave for a month– until the next party. Or, I take a second bet that I can, with the help of any guest at the party, figure out how to get out of the bondage before midnight.. If I get out by midnight, no slavery for me and you are my slave until the next party, but if I still can't get out, slavery until..."

She paused. Someone in the crowd yelled out, "A year."

Dave responded, "No, it is a safety bet. The only extra is the humiliation of an addition four hours tied to the tree during the party. Out by midnight, no slavery for Mistress Jane... or for me. If she is still there at midnight, slavery for her until the next party."

Jane nodded her head in agreement.

"That pretty much describes the bet," he answered. Then turning to the crowd around them, he continued, "And if she takes the bet and is free when you get here, she will be your host and I will be her naked, obedient slave for the duration of the party and until the party the following month."

"What are the limits," asked one of the Mistresses in the crowd.

"Nothing permanent, but other than that, no limits, no safeword," Jane answered.

A gasp went through the crowd. This was a totally slavery bet. The only limit was time.

David called out, "It is a bet! You are all the witnesses to this wager, so you are all invited to my next party, fourth Saturday of the month as usual. Arrive no sooner than 8:00 pm. We want to give Mistress Jane her full time to escape my clutches."

He then raised his drink in the air and said, "But that is for next time. For now, I believe that Mistress Robyn has a scene she would like to show us with her disobedient slave, Melinda."

As people drifted out into the yard to where a naked slave was bound to a Saint Adrew's Cross, one of the Masters pointed at Mistress Jane and said quietly to those around him, "That woman is going to end up a slave with an earful of cider."

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David sat at a table on his back patio sipping a cup of coffee. He personal valet, Harold, was collecting the breakfast dishes when David said, "Harold, would you please get an additional cup and place setting for Mistress Jane. The party is tonight. She should be arriving any moment now."

"Are you sure, sir?" he replied. "I think it was apparent to everyone at your last party that you were setting her up and that the bet was a trap."

"Yes, that was apparent to ALMOST everyone at the party," David answered with a laugh. "But what everyone else saw as my trap, Mistress Jane saw as her opportunity to trap me. Her desire to beat me in this bet blinded her to the reality in front of her. ... That and her innermost desire to be a slave, not a Mistress."

"What?" responded Harold in surprise. "I have always seen Mistress Jane as a strong woman."

"That is because you are neither a Master nor a slave, Harold, merely a devoted employee. A Master or Mistress would see the weakness behind the facade. A slave would sense a kindred spirit. I think the only reason that Mistress Jane's slave gloria doesn't feel that kindred heart is because she, herself, is not truly a slave at heart. Gloria is at heart a Mistress, not a slave."

He took a sip of his coffee and surveyed Harold's confused face. "Neither of them is aware of their true natures... yet," he said with a smile. "But I believe that will start to change at midnight tonight."

He held up a hand as if to signal for silence. "Ah, I hear the sound of a car in the driveway. You had best hurry with Mistress Jane's cup."

A few moments later, Harold ushered Mistress Jane Hendersen out the patio doors onto the patio. She was wearing a simple sundress and sandals and was carrying an overnight bag. "Good morning Master David," she said merrily as she approached the table.

"Good morning Mistress Jane," he responded. "Since you are here, I assume that our little wager is on.

"I've given it a lot of thought," she answered. "I want to see the equipment you will use first."

"Oh," he responded in a cheery voice. "I wouldn't want to totally spoil the surprise. How about two out of three? I show you the rope and the belt." He smiled at her before continuing, "We can let the sex toy be the surprise."

He turned to his valet and said, "Harold, if you would be so kind?"

Harold left and returned a few moments later with a wide, black leather belt and a coil of very thin, black rope. David took them from him and set them on the table in front of himself. "This rope," he began, "is Seal Team parachute line. It is very thin, but very strong and absolutely not stretchable or breakable– at least not by human hands. And this," picking up the wide black belt, "is a special version of a restraint belt."

He formed the belt into a loop and pushed the D-ring-like prong through one of the slots on the belt. "You can see that the tightness is adjusted by the slot in which you place the restraint connector. You press it through like that and twist it 90 degrees to lock it in place. Normally you would lock handcuffs and ankle chains to the ring, but I am not going to use it like that."

Mistress Jane smiled. She was sure what he was planning now. He would put the belt tightly around her waist and tie the cord to the restraint loop with some sort of extremely difficult knot. He was obviously relying on the sex toy to keep her distracted enough that she would not be able to get the knot loose in the required twelve hours. She had escaped at the fairs with much more distraction than that. This was going to be even easier that she thought.

"You have yourself a bet," she said loudly.

"Then let's get you tied up, shall we?" answered David.

He led her over to the edge of the patio beneath the old oak tree and said. "Take off your dress and stand here with your hands above your head."

She pulled the thin dress over her head. She was wearing nothing beneath it. As David started to tie a blindfold over her eyes, she said, "You said nothing about a blindfold!"

"Merely for while I tie you up. It comes off as soon as you are secure."

"Well..." she answered. "OK, but if it stays on, the bet is void."

"Oh, it will not stay on," he promised.

Jane then felt him wrap the belt around her. She gasped in surprise when he pulled it tight not around her wait, but at her armpits. The belt was above her breasts yet went under her arms. She felt his hands pull the belt tightly together and then push the latch buckle through and twist it to hold it in place. It pushed down hard on the top of her breasts and cut slightly into the underside of her arms, but it was not painful or unbearable.

"You think that will keep me from untying the rope?" she asked.

"Oh," he replied. "The rope won't be tied, at least not to the belt."

She felt something very light weight brush against her upheld hands. Then the rope touched her shoulders. It was being let down from above and there seemed to be two ropes, as if it was doubled over. David grabbed the rope and did something with it and then she could feel it all along the middle of her back. There were definitely two ropes, or a single rope doubled over.

David pulled the rope slightly away from her body and did something. Then he said, "Here comes the surprise."

Jane felt something cold between her ass cheeks. Whatever it was felt like a small metal ball. Then there was pressure on her sphincter and suddenly it was inside her. She could feel the cold metal ball inside her and cold metal between her cheeks and against the top of her ass. It was obviously an anal hook of some sort.

David called out, "Pull it tight, Harold." and suddenly there was pressure on her anus and tailbone and she was being pulled slightly into the air.

"You can put your hands down now," he said, and then removed the blindfold.

"That's not a sex toy," she said heatedly. "That's an anal hook."

"Ah, but it is a sex toy, and three month ago when we had out little demonstration of sex toys used in bondage, you used one on your slave, gloria. You hog-tied her with the anal hook tied to her hair so that she had to keep her back bowed even more than the tie of her legs and arms created. It was the only non-rope item you used, so you definitely thought it was a sex toy that night and I have video to prove it. You even called it your new sex toy."

Jane twisted on her toes so that she could turn herself to face David. "This is so lame," she said. "All I have to do is pull the hook out of my ass and I am free."

"Yes," David chuckled. "That is all you have to do." He then began walking around her in a tight circle. "So why don't you do that?"

Jane reached behind herself and tried to pull the intruder from her ass, but there was too much tension on the rope and she was already on tip toe so she couldn't create any slack.

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