A Lady Pays Her Penalties Read online

  A Lady Pays Her Penalties

  Ashley Zacharias

  Copyright © 2010 Ashley Zacharias

  Contents

  Forword

  The Cruel Game of Backgammon

  The Lady Gammons Herself Good

  Making a Point about Backgammon

  The Whore-for-a-Day Game

  Afterword

  Forword

  These stories are extreme fantasies about a masochistic woman named Leslie.

  This takes some readers by surprise. Everyone in the stories is a fully-informed, consenting adult. No one is killed or maimed. There are no sadists. How extreme can these stories be?

  Surprisingly extreme because they are psychologically extreme. People find it difficult to imagine that a woman like Leslie could exist.

  Sexual masochists do exist. They are described in the Diagnostic and Statistical Manual of Mental Disorders. They are not common but there are millions of them in the United States. You have probably met such a person at one time or another.

  Many sexual masochists, like myself, only fantasize about such things. Others carry their thoughts into action, using various techniques to constrain or hurt themselves. I doubt, though, that you would find a real person who is as extreme as Leslie. She is a true fantasy.

  The Cruel Game of Backgammon

  “Why backgammon?”

  “Because it has been called a cruel game and I want to play a cruel game.” Leslie smiled at her friend.

  “It’s cruel because you’re going to give yourself a penalty for losing?” Craig frowned in return.

  “No. The game is cruel in itself.”

  “How can backgammon be cruel apart from your self-imposed penalties? It’s just a dice game.”

  “It’s cruel because chance has such a large effect on the outcome. There’s a lot of strategy behind backgammon, but if you get bad rolls, you’ll lose even if you play well. The cruel part about that is that it makes you are uncertain about why you lost. That keeps poor players from getting better. They spend their whole lives playing badly and cursing the dice. They don’t even try to learn to play properly.”

  “How much does chance matter?”

  “It depends. If two people play exactly the same, then the outcome is determined completely by the dice. On the other hand if one player plays really badly and the other really well, then the bad player will almost always lose. But it’s never certain. Sometimes, the dice will be against the better player and it doesn’t matter how brilliantly she plays.”

  “Do you think that you play well?”

  Leslie smiled. “Yes, I think that I play well. Most of the time, I beat most of the people on the Internet who call themselves ‘experts’”

  “But just knowing that you win more often than you lose isn’t enough to satisfy you?”

  “No. It’s only interesting if you care about the outcome.”

  “And these envelopes will make sure that you care.” Craig nudged the three manila envelopes that were stacked next to the computer.

  Leslie’s heart skipped a beat, thinking about the instructions that she had sealed into the envelopes last night. “Yes. I definitely want to win today. I’ll play three matches against strangers on the Internet. If I lose one match, then I’ll suffer the somewhat uncomfortable and humiliating penalty in Envelope One; two matches, the rather painful and decidedly degrading penalty in Envelope Two; and if I lose all three matches? Well, I don’t want even to think about what I put in Envelope Three.”

  “And I’ll administer the penalty next Saturday if you lose?”

  “Right. If I lose.”

  “Why the six-day delay?”

  “That will give me ample time to ponder the foolishness of my bet.”

  “I’m not sure that I really understand, but, if this is how you want it, then I’ll make it so.”

  “Thank-you, Craig. I want you to know how much I appreciate your help. It’s a lot safer to have you administer my penalty than to do it to myself when I’m alone. And I can be a lot more imaginative if I don’t always have to use handcuffs and wait for ice to melt. Not every girl is lucky enough to have someone that she can trust as much as I trust you.”

  “I’m glad to help,” he replied dryly. “You know you scared the hell out of me last winter when I found you hanging from that hook in your closet. I though you were dead.”

  “I almost was.” She flexed her left hand and massaged it briefly with her right. “I don’t think that I’m ever going to get the full feeling back at the base of my thumb. Who would have guessed that the wet string would to stick to the side of the jar after the ice melted? If you hadn’t broken my back window and let yourself in when you did, I wouldn’t have lasted much longer.”

  “I never would have done that if your sister hadn’t phoned me from Phoenix and asked me to look for you. When you disappeared for two days like that, you scared her half to death.”

  “I’m so grateful for your understanding.”

  “I just want to be sure that that won’t happen again.”

  “So let’s play, already.”

  She clicked on the Play button on the screen. After a moment, a backgammon board appeared. Her unknown opponent rolled a six. The game had begun; she was committed now. Her gut knotted. It would be awfully hard to win three matches in a row. Odds were that she’d suffer some penalty for losing at least one match. When she clicked on the image of her die, it rolled to show a one. Her anonymous opponent made her bar point. “Bad start. This is going to be tough.” She rolled a five and six and had to leave a blot. The dice were against her. Her heart started beating even faster. She looked at the envelopes lying beside the computer and licked her lips. If she kept rolling like this, Saturday was going to be a long, long day.

  She lost the first match, one game to three. Her opponent played as well as her and she simply could not get the numbers that she needed.

  “So you lost one. You’ve earned the penalty in Envelope One at least.”

  The penalties that she had sealed in the envelopes were no longer theoretical. She would suffer one of them on Saturday. “Yup. Now I have to win to avoid Envelope Two or Three.”

  “Guess I’d better not make any other plans for Saturday if I have to be here watching you torture yourself.”

  “Yup.” Leslie said curtly. She did not want to discuss it.

  She won the first game in the second match, but only played half of the second game in the second match when her opponent left the game. “Coward. I would have won that one. He didn’t know what he was doing.”

  Craig looked at her. “What happens now? When the other player gives up before the match is over?”

  “That’s your choice. If you think that he quit because he was losing, then it counts as a win for me. Say, for instance, that I’d already won a game and was likely to gammon him. But if you think that he still had a good chance of winning, then you can discount it and I’ll play again.”

  “And if I think that you would have lost?”

  “Then you can call a rematch, but you can’t call it a loss. I only lose if it says so on the screen.”

  “What if you quit?”

  “Well, then I lose, of course. But that’s not going to happen. When I start something, I finish it.”

  “So what do I do now?”

  “Rematch. That was only the second game. I’m pretty sure that I would have beaten him, but I wasn’t going to gammon him and he could have been lucky in the third game.”

  “Okay. Rematch it is.” Craig thought for a few seconds. “It hardly seems fair if the players who are losing can bail out early and the good players only have to hang in for as long as they are winning.”

 
“Yup. It’s stacked against me, all right. But that’s the rules I want.”

  “Be careful what you wish for. You might get it.”

  She glanced at the three envelopes. “I hope that I don’t get worse than I deserve.”

  Craig frowned at her. “I don’t think you deserve anything bad.”

  She ignored him and rolled the dice. She got a strong start in the second match, gammoning her opponent in the first game, earning two points. But then, in the second game, her opponent doubled her early and she had to accept. Then she played too recklessly, let her men get too spread out, lost three blots to a lucky double three, and got gammoned. Being gammoned on a double game was an automatic loss for the match. She silently berated herself for playing too dangerously.

  Craig casually tossed Envelope One to the side. “If I understand your rules correctly, that means two matches lost and Envelope One is off the table. Now you’re playing for two or three.”

  “I know,” Leslie whispered, looking at Envelope Three fearfully. When she prepared the contents of that one, she had taken a delicious thrill in making it as extreme as she could imagine. It only had been a fantasy. She thought that she would never have to worry about it becoming a reality. After all, she was a good backgammon player; what were the chances that she would lose three matches in a row? Better than she had guessed, apparently. Now there was an even chance that she was going to have to suffer the agonies contained within Envelope Three.

  Her hand was shaking as she reached for the mouse to start the third match. She won the first game, lost the second to a double and was down two games to one to two. She would have to get really lucky to avoid the third envelope. A tear trickled down her cheek. She should have been more careful about what she had put into that envelope.

  Craig reached out and wiped the tear away. “You don’t have to do this, you know.”

  “Yes I do. And so do you. I finish what I start. I’m going through with this, no matter what.”

  She rolled the dice.

  The game was touch and go, but she managed to clear her inner table while her opponent still had three men on the board. The score was two up and the next game would decide her fate.

  She rolled strong dice and, by the end of the game, was well ahead in bearing off; especially as her opponent still had one man trapped in her inner table. Abruptly, a window appeared on her computer saying that the other player had left the game before it was over.

  She looked at Craig, fearful that he would make her play a rematch. “I would have won that game and the match. I was way ahead.”

  Craig smiled evilly. “I don’t know about that. It’s pretty hard to bear off without leaving a blot and if he’d hit it, he might have won.”

  “I had half my men off. It would have been hard for him to come out ahead even if he’d hit me.” She heard herself pleading with her friend. She watched Envelope Three out of the corner of her eye.

  His expression softened. “Well, I guess it’s not your fault that he chickened out when the going got rough. You’ve got the win so Envelope Three is off the table. So, you’re done. You played three matches and lost two. That means that Envelope Two is your final penalty, right?”

  Leslie nodded silently, not trusting herself to speak.

  Craig picked up the envelope with “Two” written on the outside. He looked at her with compassion. “You know, you don’t to go through with this. I’ll just tear up this envelope without even looking inside if you say the word.”

  Her expression hardened. “It’s not fair for you to say that. I don’t want to hear it again. Not ever. I made my decision before you arrived here this afternoon. I don’t welsh on a bet. Not even one that I made with myself. I trust you to do exactly what that envelope says without giving me a chance to chicken out.”

  “Okay, then.” He waved the envelope. “Should I read this now?”

  “No. Keep it sealed. When you come over on Saturday, bring it with you, still sealed. I’ll let you know when to open it.”

  “Okay, I’ll bring it back at noon on Saturday. Should I bring anything else?”

  “Nope. I have all the equipment that you’ll need. Except, you might want to bring a novel. It’ll take most of the afternoon for me to serve the penalty. It might get boring for you.”

  He smiled. “With your imagination? I don’t think you could arrange anything boring even if you wanted to. Have a good week.”

  “Thanks.” But Leslie would not have a good week. There was no joy in that envelope; she had intended that it be a penalty when she wrote it and knew that she had nothing to look forward to but a long, painful, humiliating afternoon.

  After Craig left, she slowly tore up Envelope Three and threw it away without looking at the pieces. She never believed that she could lose three matches in a row so she had been excessive when she’d designed the worst penalty. Unrealistic. She had barely managed to win the third match. Next time, she would be a lot more careful about imagining what she could tolerate if she was that unlucky again.

  When she finished disposing of the other envelopes, her thoughts turned to the one that Craig had taken with him. Would she be able to bear the pain of the things that she had enclosed there? It did not matter. As long as Craig held up his end, she would pretty much be helpless, unable to stop the penalty until it was complete. On Saturday she would have no choice but to tolerate everything that would happen to her, even if it turned out to be intolerable.

  * * *

  When Craig arrived just before noon on Saturday, he noticed that all her curtains were closed; no one but Leslie and he would know what happened in her house today. He rang the doorbell. When Leslie answered, she was wearing a sweat suit.

  Craig was vaguely disappointed. He had imagined something more exotic; that she would be dressed in leather or rubber or something.

  Leslie did not smile. “Hi. Craig. Thanks again for helping me with this.” There was a tremor in her voice; she sounded afraid. She continued, too quickly for him to respond, “Please come in.”

  “Thanks.” When he stepped across the threshold, she closed and locked the door behind him.

  “Have a seat in the living room.”

  When he was seated, he waved the envelope in his hand and asked, “So I open this now?”

  “Not yet. I have to go upstairs and get changed. While I’m gone, I’ve got something else for you to read.” She handed him a folded piece of paper. “This is a tricky thing. Please don’t be insulted by it, but it’s something that you have to understand before we can proceed. I’ll be back in ten minutes.”

  She left the room.

  Craig frowned as he unfolded her letter. It was handwritten. Her script was clear and neat. She was a highly organized person.

  The letter read:

  Dear Craig:

  We do not have a sexual relationship; we are happy as platonic friends. And I understand that you intend to remain faithful to your wife. I respect your integrity. But I have to be realistic about one thing. In the course of this afternoon, I will make myself helpless and vulnerable. I do not want to be raped; I do not expect to be raped. That is not part of my penalty.

  But I have to recognize that you are a man with a normal sexual drive. My vulnerability cannot help but put considerable stress on you. If, despite you best intentions, you find that you are unable to restrain yourself and you exceed my instructions – to be blunt, if you find that you have raped me despite our understanding – then you must realize that there will be no consequences for you. I am taking responsibility for your actions before we begin. It is me who put you in this position and I will never tell anyone, including your wife or my best friend what happens. After all, what could I do about it, anyway? There’s no way that I could ever bring myself to tell anyone that I am such a pervert that I put myself in bondage in your presence.

  As a compromise, if you are compelled to relieve yourself and don’t want to penetrate me, you are welcome to do so, either in my presence or priv
ately, I will understand and be grateful for your restraint in not going further. Again, to be blunt enough to ensure that there is no misunderstanding, if you feel compelled to jerk off on me, feel free. I don’t expect it and don’t want it, but if you do, I will not think any less of you. I know that whatever happens will be my fault for having put you in such a hard position (pun intended).

  Please take this letter with you and keep it somewhere safe for long enough that you can be assured that there will be no consequence for helping me, no matter what happens.

  Your dear friend,

  Leslie.

  Craig folded the letter thoughtfully and put it in his shirt pocket. He was mildly insulted that Leslie thought that he would fly out of control just because she was likely to be tied up and naked in his presence. Contrary to the assertions of some radical feminists, most men are not beasts and rapists. She should certainly know him well enough to know that he was stronger than that. On the other hand, he had to admit that she was right to write the letter. From her point of view, if she had misjudged him and he did rape her when she was helpless, she had to reassure him that it would not be a problem. Otherwise, there was a risk that he might, in a fit of shame and fear, kill her just to try to hide what he had done. He understood that she had no choice but to give him this letter for her own protection.

  Leslie was nothing if not thorough. Still, even though he could understand and agree with her logic in giving him the letter, he could not help but feel the sting of an insult.

  A few minutes later, Leslie re-appeared in the doorway. This time she was fully clothed in a knee-length, navy, pleated skirt and white blouse – conservative clothing. Incongruously, she was also wearing black hose and black high heels – probably the highest heels that one would find in a normal shoe store – not so high as to be outrageous, but high enough to be impractical. Craig was sure that Leslie, who normally wore athletic shoes, even to work, would find these stiletto heels decidedly uncomfortable if she had to stand in them for long.