A Lady Plays for High Stakes

By Ashley Zacharias

Leslie is playing backgammon again. As a sexual masochist, she delights in designing severe penalties for herself that she must pay if she loses the game. This time, the stakes are higher than ever. Her husband is appalled by the punishments that she risks if she loses. But she demands that he fulfill his part of their agreement, no matter how severe the consequences. These three novellas feature kinky BDSM scenes, which include bondage, humiliation, and torture. If you don’t like reading about such things, this book is not for you.

• Language: English
• Publisher: Ashley Zacharias
• Release date: Mar 30, 2015
• ISBN: 9781311788146

Ashley Zacharias

I am a post-modern woman who lives a vanilla life but fantasizes about adventures in masochism. I appreciate readers who purchase my books but, more than money, I need your honest response to my writing. Review my books or contact me at ashleyzacharias.com and let me know what you think of my stories. Good or bad, as long as you are not indifferent, your honest response will help me to write more and better stories.You can find my thoughts about my own stories athttp://ashleyzachariascommentary.wordpress.com/Yours, Ashley

Book preview

A Lady Plays for High Stakes

by

Ashley Zacharias

Copyright (c) 2015 Ashley Zacharias

All rights reserved, including the right of reproduction, either in whole or in part, in any form. This book is a work of fiction. Names, characters, places, and incidents are either products of the author’s imagination or are used fictionally. Any resemblance to actual persons, living or dead, is entirely coincidental.

Smashwords Edition, License Notes

This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away. If you would like to share this book with another person, please purchase an additional copy.

Contents

Note

The Whore-for-a-Day Game

Backgammon Redux

Backgammon Grudge Match

Afterword

Note

The previous editions of A Lady Pays Her Penalties and A Lady Plays for High Stakes differed from these editions in two ways.

First, The Whore-For-A-Day Game was previously included in A Lady Pays Her Penalties. For better thematic consistence, it has been moved into this volume, A Lady Plays for High Stakes.

Second, two short stories, The Key to the Woman and On the Flip of a Coin, that were included in the previous edition of A Lady Plays for High Stakes have been removed because they are not about Leslie, Craig, and Alex.

These changes will only be noticed by someone who read the early edition of A Lady Pays Her Penalties and discovered that The Whore-For-A-Day Game has been repeated in A Lady Plays for High Stakes. If you are such a reader, please be assured that you have not mistakenly bought the same book twice. Nor have you missed any of the stories about Leslie and her friends.

If you would like to read the two short stories that were removed from this volume, they can be found on the web at http://ashleyzachariasarc.wordpress.com.

Yours, Ashley

The Whore-for-a-Day Game

Let me be blunt, Alex said. We’ve been married for more than a year and a half and it’s not as good as it should be. I’m willing to do whatever it takes to have a better marriage. I just don’t know what I should do.

I think everything’s fine, Leslie said, but there was no conviction in her voice.

Alex waited for a long time, hoping that she would elaborate, but she remained mute. Eventually he asked, Are you happy?

Yes. Are you?

Not especially. Not as happy as I thought that I’d be when we first got married.

Well, I guess life isn’t a bowl of cherries after all, is it?

I’m not sure that it should be this sour.

She looked at him with shock. You think that our marriage is sour?

It’s not sweet. You can be pretty sarcastic sometimes, you know.

Is that it? You want me to act sweeter. You don’t want me to be so sarcastic? I can try to change that if you want.

It was his turn to look at her for a while, trying to figure her out. I don’t think that’s it, he said, finally. I don’t mind your being sarcastic. I just think that we’re stuck in a rut. We don’t have as much fun as we should.

You think we should have more fun? Like what? I’ll do whatever you want to do for fun. Go dancing? Go to more movies? Whatever.

It’s not that simple. It’s… I don’t know. It’s something more important than that.

She looked at him through narrowed lids. Okay. Let’s do it this way. I think that our marriage is fine. You don’t. You said that you wanted to be blunt, so be blunt. Tell me exactly what you want that you’re not getting.

He blushed, and then said, Okay. Let’s start with sex. I think that we should have more sex.

You think that we should have more sex or you want more sex for yourself. This is important, so let’s be absolutely clear about this.

I want more sex. I love making love to you. There’s nothing in the world that I’d rather be doing than making love to you. Nothing.

And doing it whenever we feel like it isn’t enough?

Three times last month? That’s not much sex, you know.

It was her turn to blush. You’re keeping count?

It’s not like it’s hard for me to count to such a big number.

And you call me sarcastic. So what do you think would be a good number? Twice a week? Three times?

That would certainly be a better number.

Even if I don’t feel in the mood? Even if I can’t enjoy it?

No. I want you to enjoy it as much as I do. I don’t want to make love to you if you’re not having any fun.

So that puts us right back where we started. I’m happy; you’re not. And if I’m not happy, then you’re still not. I’d say that it sounds like you have the problem, not me.

He sighed. I don’t think that you’re being honest with me. I don’t think that you’re really as happy with the status quo as you claim.

What makes you say that?

The way you act with me. You don’t act happy.

Maybe I don’t want to be happy. Maybe I’m happy not being happy. Did you ever think about that?

Now you’re being sarcastic with me again.

She paused. Then she said something strange. No. I’m not being sarcastic. I’m being literal. You’re going to think that I’m all screwed up in the head, but sometimes I need to be unhappy. Sometimes a little dose of misery is exactly what I need. She paused and he saw that her hands were trembling. I… God, this isn’t easy for me. I… She stopped and looked at him. There was a glint of desperation in her eyes.

Have you had an affair? he asked softly.

What? No! God, no! I haven’t slept with anyone but you since before I met you.

Do you want to have an affair? His voice was soft. He considered the possibility that she didn’t make love to him often because she didn’t enjoy it. Maybe she’d be happier making love to another man. Maybe she’d be happy making love to someone else more often than she made love to him.

That thought hurt.

No! Never! How can you even ask that? How can you even think that? There was outrage in her voice.

The way you were talking about feeling miserable, I thought maybe that you were hinting that you were feeling guilty about having an affair.

No. It’s not that. Not at all. I… She paused again, searching for the right words, then slumped in her chair in defeat.

Okay, babe. Okay. There’s something else then. I promised myself that I’d never raise the subject, but maybe I have to. You can tell me if I’m out of line, and I’ll stop talking and never mention it again but maybe we need to get this out in the open. He paused to collect his thoughts then said, carefully, Back when we first started dating, there was a time, once, when you asked me to use you sexually without considering your feelings. In fact, I believe your exact instructions were to treat you like a piece of meat. I tried to do what you wanted. You made it clear, though, that you didn’t want to be treated like that normally, that it was a rare thing. Like a one-time thing. Is that what you’re talking about? If it’s not, just let me know and I’ll never mention it again. But now you’re making me think that you need something like that again and I’ve been too dense to realize it and treat you like that.

Leslie couldn’t meet his eyes when she said, No. You’re right. I have needs. Needs that I don’t like to talk about. Sometimes I need to be treated badly. Sometimes I need to feel miserable to be happy. I know that it isn’t normal. I’ve been afraid to tell you because I don’t want you to think that I’m weird. Worse, I’m afraid that, now that I’m telling you, you’re going to think that you should treat me badly all the time and that’ll ruin things for sure. Those things are too intense to do more than on rare occasions. You saw me once on one of those rare occasions. It’s been two years since we did that. I think that I’m past due for another session.

You want me to do the same thing to you that I did that night?

No. She looked thoughtful. Something different. I need a lot of variety.

What?

I’ll think of something and let you know. Now, can we just go to bed and make love like normal people and pretend that we have a happy marriage?

If that’s what you want.

That’s what I need today. Soon, maybe tomorrow, maybe next week I’m going to need something different.

Let me know.

Count on it.

* * *

On Monday morning, Alex found an envelope on the table next to his breakfast. That was the third surprise of the morning.

The first surprise had been that breakfast was waiting for him. Leslie never ate breakfast so Alex normally had to microwave a bowl of instant oatmeal for himself.

The second surprise was that Leslie had gone to work before him. She’d waved at him as he was coming down the stairs and said that she was going to go to work early today, then left. Usually, she left at the same time as he did.

It was clear, now, that she’d cooked his oatmeal while he was getting dressed and had waited for him at the bottom of the stairs so that she could say goodbye before running out.

If the envelope itself was the third surprise, then the letter it contained was the fourth, and biggest surprise, not just of the morning, but of his entire marriage. It read:

Dear Alex:

You say that you want more sex. Okay. Next Saturday, I’m going to give you all the sex that you want and more. I love to play games so I’ve made up a new one. It’s called the Whore-for-a-Day Game.

For twenty-four hours, I’m going to be The Whore and I’m going to have only one client: you. You’re going to be two people. At eight o’clock on Saturday morning, you’re going to be Leroy, the Pimp for a few minutes and turn me out to be your whore. Then, for the next twenty-four hours, you’re going to be John, the John, my one and only client. Finally, starting at eight o’clock on Sunday morning, you’re going to be Leroy the Pimp again.

Like any game, the Whore-for-a-Day Game has rules. The most important rule is that The Whore has a quota to fill. To make her pimp happy she has to earn a certain amount of money. But, to make the game interesting, neither The Whore nor Leroy/John knows what the quota is. The Whore and Leroy are going to roll a single die but they’re not going to look at it. Maybe they’ll roll a one, maybe a six; they won’t know until they look at the die on Sunday morning.

For twenty-four hours, The Whore is going to have to make John have as many orgasms as she can. That’s what whores do – they do whatever it takes to get men to have sex with them as often as possible. And they charge for their service. Every time John has an orgasm, he’s going to pay The Whore $100. That’s what johns do – they pay for it. John better make sure that he starts with $600 in cash in his pocket because The Whore is going to try her damnedest to earn every penny of it.

It’s going to be pretty easy for The Whore to earn at least a hundred dollars because you’re prohibited from jerking off between now and Saturday morning and I’m sure as hell not going to have sex with you before then. If you have even one orgasm between this moment and Saturday, then you are honor-bound to tell me so that I can cancel the game. I advise you to spend the next few days trying not to think about sex.

On the other hand, it’s going to be damned hard for The Whore to earn all six hundred dollars because that’s a lot of orgasms for one man to have in twenty-four hours, even a man who hasn’t had sex for five days.

Let me be perfectly clear. John does not have to please The Whore in any way. He does not have any obligation but to please himself. In particular, he does not have to have sex with her if he’s not in the mood. It is totally up to The Whore to put him in the mood and bring him to orgasm as often as she can. John’s frequent satisfaction is her job, not his.

She will want to do a good job.

Remember, The Whore has that damned quota on that hidden die to worry about. Every whore needs an incentive to work hard. On Sunday morning when The Whore reports back to Leroy with her hard-earned cash, they’re going to look at that die together. Every spot on the die is worth a hundred dollars. If she has earned her quota, then she keeps the money and Leroy takes her shopping so that she can spend her money on a nice gift for herself. But if she fails to make the quota, then Leroy’s going to be angry. He’s going to take all the money away from her and then he’s going to punish her from eight o’clock Sunday morning until noon. He’s going to tie her up and beat her and abuse her terribly. If his Whore was lazy and useless, Leroy will make The Whore suffer in misery for four long, long hours.

Love, Leslie (soon to be your whore)

Alex pushed his porridge aside. His appetite was gone. Completely forgotten. He read the letter again, and then a third time. Common sense was telling him that this was insane but his dick was singing a different tune; it was as hard as a rock. He wanted nothing more than to run upstairs and jerk himself into ecstasy. But that would be cheating. The letter was clear about that. From now until Saturday morning, he wasn’t permitted a single orgasm.

If he played by her rules, he was facing five days of severe frustration. She had written a letter that was guaranteed to set him on fire at the same time that it denied him any relief. Had Leslie planned it that way? Was this her way of punishing him for complaining about not getting enough sex? She was a smart girl. And she loved her cruel games. She knew what she was doing when she put Alex in this predicament. It was no accident.

He read the letter for the fourth time. She was facing the possibility of spending four hours in hell; he was facing the certainty of spending five days there. What was fair about that? For a brief moment, he thought about cheating. If he jerked off three times a day every day until Saturday, John would be exhausted. The Whore wouldn’t be able to earn even a hundred dollars.

He dismissed the idea as soon as he thought about it. She would be watching him and, if she caught him, the game was off. He dearly wanted to play her game.

And even if she didn’t catch him, what would be the fun in a predetermined outcome? He wanted to see how the game turned out when it was played fairly. Making him come six times in twenty-four hours would be a challenge. How many wives would accept that challenge? He was thrilled to know that he had married a woman who would suggest such a thing.

And if she succeeded? He would respect her accomplishment for the rest of his days.

He took his pen from his pocket and scrawled, You’re on. We start playing at eight on Saturday morning. Good luck. He left it on the table for her so see when she came home from work tonight.

He was going to have to throw himself into his own work wholeheartedly for the next few days to distract himself from thinking about the Whore-for-a-Day game. Yeah. Like that was going to work. He knew that he would be unable to think about anything else. For five days, he would think about nothing but sex with his wife and would have to master his desperate desire for her by sheer force of will.

For him, the game had already begun.

* * *

On Saturday morning, Leslie kept her alarm set for seven o’clock, the same as on weekdays. On working mornings, she rose first and took her shower, expecting Alex to roll over for another fifteen minutes.

But today was different than any other Saturday. Alex had lain awake long before the alarm rang, waiting impatiently for the Whore-for-a-Day Game to begin. For most of the night, he had been sporting a huge erection. He dared not touch himself for fear of releasing an earthshaking orgasm that would drench the bed and cancel the game. He kept telling himself to be strong. Wait and there would be orgasms aplenty a coming. Much better orgasms than he could give himself.

Another difference was that today, Leslie had shaken him to make sure that he was awake and told him that he could get up and shower right away. She was going to use the main bathroom and leave the en suite to him.

Showering without stimulating himself was just one more ordeal capping a week of the same. As on the previous five mornings, he managed to stay strong. And erect. It took no small effort to get his jeans zipped up without creaming them. Eight o’clock couldn’t come soon enough for him. The way he felt, The Whore could earn her first hundred dollars just by brushing her fingertips across the outside of his pants.

Earning her second hundred dollars might be almost as easy.

When he came downstairs, he found Leslie in the kitchen, cooking bacon and eggs. To his amazement, she was dressed like a housewife from fifty years ago. She wore low black pumps, a calf-length black skirt and modest white cotton blouse. To top it off, she was wearing a red and white checked apron and a double string of pearls. Pearls. He didn’t know that she owned pearls, much less would wear them while she cooked breakfast. He caught a glimpse of matching pearl earrings when she flipped one side of her long brown hair off her left shoulder.

The outfit should have been demure, but something in the way her lovely breasts filled the blouse and her cherry red lips parted in a teasing smile almost made him come in the middle of the kitchen. She was the sexiest housewife he had ever seen. And she was his sexy wife. For a brief, mad instant, he thought that he should tell her to forget the game and get back to bed for some regular, married, perfect, Saturday-morning sex.

Instead, he sat down and waited for her to serve breakfast.

They spoke little as they ate. When Leslie finished, she rose and said, I better get the dishes done. I’ve got an appointment with a man named Leroy. Apparently he has some kind of business proposition for me. He should be arriving at eight. I’ll be waiting for him in the living room. Please send him in when he arrives.

I’ll make sure that he knows where you are.

Ten minutes later, at exactly eight o’clock, Alex found Leslie sitting primly on the living room sofa, waiting patiently. When he sat in the easy chair across from her, she said, I’ve been told that you have a business proposition for me, Mr. Leroy.

That’s right, Alex replied. I believe that you could have a lucrative career in sales.

In sales? That sounds interesting. I could meet lots of people that way.

Yes, you certainly could.

What would I be selling?

Why, yourself, my dear. It’s been said that every salesman ultimately sells himself. You would be doing that quite literally.

She frowned. I don’t think I follow your meaning.

I propose to employ you as an escort.

She looked shocked and raised her fingertips to her mouth. An escort, sir? Do I understand that you mean to make me a whore?

Yes, dear. He gestured at the generous breasts that were pressing against the too-tight blouse. You appear to be naturally inclined to the profession. If you apply yourself, you will find my proposition to be quite lucrative.

Indeed? How much do you think a man would pay for my services?

I recommend that you charge a flat rate of one hundred dollars.

My, that is a lot of money. What would I have to do for a hundred dollars?

Whatever it takes to satisfy your client.

In my new profession, my clients are called ‘johns’, are they not?

That they are, dear.

How many of these johns would I have to service in a night?

As many as possible.

How many would that be?

Alex Leroy raised an eyebrow. That’s up to you.

I guess that I’ll just have to do the best that I can, then.

That’s all I ask.

Leslie – now The Whore – opened a small chest that was sitting on the coffee table and removed two small padlocks, a large white die. I guess I’ll just have to trust to chance that I’ll be good enough, won’t I?

Try your luck, dear.

She put the die in the chest, closed the lid and rattled the die inside for a long time. Her breathing was fluttery and Alex could see a lovely dew of nervous sweat on her upper lip. Then she the chest down with the die trapped inside. Neither one of them had any idea which side was face up. The chest had two hasps. She snapped a padlock through each hasp and held one key out to her new pimp. You’ll want to put that key in a safe place until you need it tomorrow morning. She kept the other key for herself. As long as each held their own key, neither of them could open the chest to inspect or alter the roll of the die.

Now, if you’ll excuse me, Mr. Leroy, I would like to find my first john and get to work as soon as possible.

She left Alex sitting in the easy chair, stunned that the game had actually begun. He was going to have as many orgasms as he could manage in the next twenty-four hours. But right now, he cared only about getting the first one done as soon as possible. He was about to explode in his pants. But he didn’t want to do that. Now that the game had begun, that would count as one score for The Whore. She could legitimately demand a C-note even if she wasn’t in the room. After all, she would be correct in claiming responsibility for his excited state.

Before he could finish the thought, The Whore was back. She was still wearing her housewife outfit, from pearls to pumps. Why Mister, she said, you look awfully stressed. Hasn’t your wife been treating you properly the last few days?

"No, I can’t say that she has.

Well, for a hundred dollars, I can do something for you what she won’t. What do you say?

I’ve got a hundred dollars right here, Miss. He pulled a hundred-dollar bill from his wallet. He had gone to the bank days ago and withdrawn six of them.