The bet (drained to the lees)

Alex was addicted to gamble. He was enjoying the game not for the win but for the thrill of playing.
He was challenging his friends for insignificant reasons just to provoke an encounter.
His favourite phrase was “For how much?”. But he wasn’t playing only for money.
He could duel just for a glass of whiskey or even a woman’s French kiss.
The amazing thing about his passion was that he had won almost every bet he had taken.
He was boosting to his friends about his achievements and challenging them for more.
His other notorious virtue was his self-control.
He was able to dominate over his emotions, from joy and happiness to pain and distress.
For instance, he could stand immense body or mental tortures without a wince, as well as ferocious tickles without a little smile.
His gambling vice joined to his self-controlling ability, was an odd yet very effective combination.
But all his world of confidence and supremacy was about to collapse.
It was a usual midweek afternoon pleasantly spent with his usual friends from the office at their usual after work bar.
He had drunk a few beers (maybe more than a few) and was getting ready to leave for home.
Then the voice of Betty, one of his not so close colleagues reached his ears:
“Dear Alex, I might have a challenging situation for your betting habits.
There is a lady that is eager to confront you and ready to bet she will win over the stake.
Because of the delicate nature of the wager she gave me her mobile in case you personally decide to get in touch.
She promised though that if she loses the bet she would make it public, awarding you the honours.
If on the other hand she wins, no one will ever know… ” she added with a tone of mockery and hand him a little card.
Alex never really liked Betty. He thought she was pretentious and unreliable.
He also thought she was ruthless and willing to step over dead bodies in order to ascend in the business hierarchy.
So, his first thought was to drop the card. But with a strange urge he shovelled it into his pocket.
Later that evening, sat in front of the TV, Alex thought that the rest of the day would turn out really boring.
He looked at his watch. It was just a few minutes past 8. Suddenly, he remembered the little card lying in his pocket.
He fumbled for it and got rather surprised when reading the few words typed on it:
“Contessa Fiona, emotion management expert”
”What in the world was that job qualification?” he thought. Being more curious than reserved by character, he quickly dialled her number.
“This is Alex K. Betty’s colleague” replied to her velvet “hello”
“I wonder if…” he tried to continue.
“I am expecting you in an hour at my place at…” she interrupted him without hesitation.
“Do not be late, we need all the time we can get” .
It sounded like an order to him. His first reaction was once more not to bother with that lady anymore.
But after another 20 minutes of utter boredom, he convinced himself it was worth to pay a visit to that strange woman.
He quickly got dressed and run to his obsolete car. Half an hour later, he was ringing at her doorbell.

She left him waiting for more than 1 minute. He was ready to leave the place,
when she suddenly opened the door and with a fake smile she addressed him saying:
“My my, I thought you have the reputation of a notorious gambler! A gambler without patience is a lost man…”
she exclaimed with gleeful laughter.
She was already rushing him in the house grabbing him by the elbow.
“Please sit down and make yourself comfortable, can I get you a drink?” she asked by pointing to him a cosy chesterfield armchair.
“A double scotch on the rocks would be nice” he replied feeling more comfortable and relaxed.
After fixing him the drink, she took a chair and sat face to face with him, leaving him the time to examine her thoroughly.
She was an impressive figure, not doubt about it. Long auburn – red hear, deep penetrating eyes,
flaming scarlet lips, white pale skin and the most gorgeous big beautiful body he had ever laid eyes on, all dressed in black.
She wasn’t even remotely his type of woman, the classic babe blond fragile bimbo.
“Whenever you feel ready we can discuss about the rules of our little bet” she giggled.
His eyes sparked, his lips went dry, his heart started to beat faster. His passion overwhelmed him.
“What kind of bet do you have in mind?” he asked with an eager tone of voice.
“Do you find me attractive?” she briskly asked.
“Well, as a matter of fact, to be honest…” he started mumbling but was soon interrupted:
“I thought so, so it will be an even bigger challenge to make you
cum repetitively for me, lets say 5 times in 2 hours?”. Her words were like a loud smack to his face.
“What in the name …” only got able to stutter.
“Here are the rules of our game” she replied briskly.
“You will be restrained from hands and feet, almost immobilised.
I then will be given 2 hours time to make you ejaculate in series, 5 times I think is fair enough.
It will be permissible for me to do whatever I want with your entire body, but not allowed to directly fondle your penis,
unless you plainly entitle me to.
I can use any kind of equipment, not living you permanent marks though and you are permitted to stop me by saying “mercy”,
whenever you cannot stand the emotions provoked –pain, pleasure, lust, desire, pressure relief-.
If stopped three times, then I am granted a “cuming” point.
It is also fairly agreed that no point could be gained by only provoking continuous pain to you.
If I manage to induce 5 consecutive blows, I win the bet and therefore granted lifetime permission to consider you
as my slave from then on and therefore use you in every way that I desire.
If on the other hand I fail, you are entitled to demand and legally obtain the one element of my property you fancy more,
from my sports coupe to my beach house, my jewellery collection, or my bank account.
Do you consider it a fair bet?” she concluded with flamboyance and paused to carefully observe his overwhelming reactions.
He was speechless, his mouth wide opened by surprise, his veins ready to burst from extreme blood pressure,
his eyes dark from anger, his forehead sweating from intensity.
He stayed in silence, immovable for quite sometime, measuring her,
contemplating about the pros and cons trying to decide the next move. She thought it was time to proceed.
She stood up without a word, vanished behind a door for a minute or two, appearing again holding a large bag.
She laid it before him and stood on the side provocatively, waiting for him to decide.
His passion overcame his restraints.
What the heck he was famous for his self-controlling skills and who knows he could end up with a new car!
Moreover it seemed almost impossible to feel like cuming for that woman and moreover by not being forced to.
“All right” he finally agreed, “but if you try to delude me, my revenge will be devastating.” he warned her.
“Don’t worry, no such possibility exists” she answered with a great tone of confidence in her voice.
She was already arranging the equipment extracted from her bag by a table next to her.
When finished she turned to him.
“Time to fix you too…” she mocked and gently taking him by the hand, she drove him to a corner of the room.
Next thing, he was tied hand and foot by wrists and ankles from chains hanging from the ceiling and links fasten to the floor.
She unbuttoned his shirt, then unzipped and lowered his trousers.
He was standing half naked, immobilised, inert in front of her, exposed to her wills.
For the first time in his life he wished he hadn’t taken that bet.

She firstly blocked his eye view covering all his head with a thick, double folded black woollen jacket of hers.
The sense of the fabric, combined with the body odours and perfume emerging from the worn garment,
caused him his first erection of the night.
She noticed it with pleasure. She whispered softly in his ear:
“You like being in captivity, feeling the mistress’s clothing on your face, being totally disposed to her wills, don’t you?”
He was thrilled, beyond his expectations as a matter of fact.
Her hand was now caressing his buttocks with subtle moves, approaching his upper thighs, not touching though the forbidden area.
He couldn’t resist anymore as he thought, “I have 5 rounds,I can afford to waste one or two, I might enjoy it a bit more!”
and he leaned himself on purpose towards her, trying to rub his cock against her body. “Do you feel like you need a relief?”
she asked with a teasing laugh.
“Oh yes please”, he replied and gracefully accepted the embracement of his manhood by her artful glove wearing fingers.
He came in no time. She quickly removed her hand, already studying her next move. “Round one was easily won.
The next 2-3 rounds will not be so easy, as he is not feeling so tense anymore” she thought.
He, on the other hand wasn’t preoccupied yet.

After a few minutes that she left him wondering about the next stages unable to see her manoeuvres,
she attacked his nipples from behind. She was teasing them, pinching them, tickling them, observing his reactions.
He first tried to avoid her contact by swinging his body back and forth, left and right.
When her embrace became firmer, he was left with no other option than enduring her attacks silently and patiently.
But his resistance was getting lower and lower.
By the time she heard him breathing heavily, his nipples were flame-red and intensely protruding.
He let his head fall over her shoulders. She started caressing his neck with her tongue, while lowering one of her hands under his belly.
“I ask permission to touch you” she whispered cattily.
“Oh yes please” was once more the only words he could stutter and let himself go in her palm once more,
only a quarter later from his first explosion. Round 2 were over and he began shivering not from anxiety but from strain.
Five minutes later, he was on fire. He felt the hot wax running all down his nipples, his belly, his pubic area.
She was using different kind of candles, enjoying his hopeless efforts to distance from her.
When he believed she had stopped, she was changing her position, coming from behind, deluding him, continuing her work.
His impulse was getting even bigger by the pain. 10 minutes later he couldn’t help but to cry for “mercy”.
She stopped at no time. Suddenly a feather started tickling his exhausted body.
His armpits, his thighs, his palms even his immobilised toes, were teased without mercy.
A few minutes later, her fingertips took initiative, running up and down fumbling all over his body, except the forbidden area.
He resisted only a few more minutes. His cry for “mercy” was inevitable. Once more the action was stopped abruptly.
One hour was left before the bet was over. Next thing, he felt two clips squeezing his nipples.
Before even leaving a sound of pain, the first voltage discharge hit his guts.
He was dancing to the rhythm of her wills, as she was playing with the switcher holding in her hands, enjoying with small giggles her work.
He was about to collapse, feeling his chest as if it was torn apart.
The third “mercy” was the only way out. It was said, making the sound of a bell announcing the end of round three,
45 minutes left to decide about the winner.

He was a wreck all right, ready to faint. She couldn’t give him that chance, she had no time to waste.
It was his asshole’s turn to discover her moods. She lubricated it carefully, then penetrated it slowly with her fingers, one, two three of them
getting in and out, trying to fumble his sensitive gland more and more effectively.
When she finally got pretty certain she had the situation in hand, she made her moves more accurate,
leaving him very narrow margins to escape from another involuntary yet immense blow of his penis.

Only a step away from defeat, he was then unleashed and guided to the comfortable armchair, half an hour before time elapsed.
He felt to pieces, a human wreck. He was left there for some time, then her commanding voice brought him back to reality,
while she was picking up the jacket from his sweating face, releasing all his senses:
“I am going now to unbutton my long black woollen cardi, revealing all my beauties in front of you.
Then I am going to stand right above you, and I want you to fix your eyes on my divine body and masturbate for me.
You won’t stop until you cum for the last time this evening, my NEW UNIMPORTANT LITTLE SLAVE.
Then I am going to brand your chest, just to verify you belong to me from now on”
she commanded and started approaching him, her cardi waving behind her, already half opened.
It didn’t take him more than 2 minutes.
He then stayed immobile, defeated by his own hands, patiently expecting to be branded like the new calf of Mistress’s herd.