A Lady Pays Her Penalties

by Ashley Zacharias

  Leslie was less lucky with her next opponent; he played extremely well better than her and good players tend to win at backgammon.

  She had a man on the bar and only one point open on his inner table he doubled her. She was ahead in pips, but was likely to waste a lot of rolls trying to get back into the game. She looked at the two envelopes in Craig’s hand. If she took the double and lost, the day would be over and she would be paying a full six penalties next Saturday. If she took the double and won, she would get rid of the Envelopes Three and Four and be back on safe ground.

  She looked again at Envelope Five and Six. Craig gave her an evil smile and waved them at her. There was a fair chance that she would win if she accepted the double, but as much as she hated to accept Five, she dared not risk getting stuck with Six as well.

  She clicked the Resign button. Her hand was shaking visibly as she added the fifth envelope to her pile.

  “Are you going to quit while you are ahead?” Craig asked.

  She was stuck with five envelopes, but if she tried to get rid of them, she risked a loss and that would mean having to pay all six penalties, including the one that she said that she would never risk serving.

  “I’m going to think about it,” she said quietly and sent a “Sorry, I have to go now” message to her opponent.

  She sat in silence for a long time, staring at the five envelopes in front of her. Her hand was trembling as she flipped through them one at a time, remembering what was in each. Then she looked at the sixth envelope that was still in Craig’s hand. If she played one more game and won, she could get rid of Envelope Five. That would be a small blessing. But if she played again and lost, she would be forced to obey the instructions in Envelope Six. That would be unthinkable.

  When she made up the envelopes last week, she had promised herself that, no matter what, she would quit before she risked suffering the fate that she had stuffed into Six. Even if she were ahead in a game, and were offered a double, she would not accept it if it would put that envelope into play; even if she were certain that she could win. That’s what she had told herself last week. Now, though she was face-to-face with the question for real. Could she make herself pay the penalty in Five without at least taking the chance to escape it? Five was awful. Was Six that much worse than Five?

  “I want to take a break and think about my options,” she told Craig and walked toward the door on legs that were quivering so badly, she was afraid that they would not hold her.

  “Take your time,” he replied to her back, feeling sympathy for his friend’s obvious fear. Then he reminded himself that whatever was in these envelopes, she had arranged the situation for herself. Nobody had forced her into anything. And she knew damned well that she could tell him to forget about the whole thing, throw the envelopes in the trash, and he would happily forget about it, never knowing what she had written. Nobody was going to force her to do anything. Nobody but herself. But he knew perfectly well that she would force herself to go through with whatever she had put in those envelopes, no matter how badly it hurt her. She was an exceptionally determined woman.

  She had a self-destructive streak and he had to ask himself if he was morally wrong to enable it. Possibly she was imposing worse penalties on herself and taking greater risks just because she knew that he was there to rescue her if she went too far. But there was a limit to what he could do if she got into some kinds of trouble. He did not want to be a witness if she maimed herself, or worse. Maybe if she had known that he was not going to be there, then she would have been more careful about what she wrote in the envelopes. But, now that he was here, he was trapped; if he refused to help at this point, she would do something dangerous anyway. She had tried playing solo before and almost died when a string accidentally stuck to the side of a wet jar. He had to stay with her and keep her as safe as he could while still letting her suffer as much as she wanted.

  He could only hope that what was in the fourth and fifth envelopes was not too dangerous.

  When she returned a few minutes later, she looked composed, but her face was distinctly gray. She had washed off what little makeup she had been wearing.

  “I’m going to go for it. I think I can win.” Her voice quavered in fear as she spoke her brave words.

  Her decision was as predictable as dawn. Leslie was as stable as a rock in most aspects of her life, but when it came to self-punishment, she would take the gamble every time.

  Her next opponent played a high-risk strategy, hitting her men in her inner table, leaving blot after blot exposed. She popped back on the board again and again, sending his men to the bar, but he made the occasional lucky roll and his strategy began to wear her down. First he made one point in his inner table, then another, limiting her ability to get back off the bar. And she had been so busy getting back on the board that she had had no opportunity to make points in her own inner table. When he managed to make the fourth point on his inner table while she still had a man on the bar, he doubled her. She was far ahead in pips, but would have difficulty getting back on the board. Any other time she would refuse the double, but not this time. This time, if she refused, she would automatically get Envelope Six and the game would be over; but if she accepted, she would do no worse than that – there was no Envelope Seven to worry about.

  She accepted the double.

  And she lost the game.

  She could barely see the computer screen through her tears as she made her last desperate moves.

  Craig had a hard look on his face as he handed her the last envelope. “Here. This is what you want. I hope you enjoy your week.”

  She handed the stack of envelopes back to him. “You hold on to these. The temptation to alter them might overwhelm me if I keep them,” she said in a watery voice. “Can you be here at eleven o’clock on Saturday?” Tears overflowed her eyes.

  “I can.” He carried the envelopes away, leaving her to weep alone in her misery.

  * * *

  When Craig knocked on Leslie’s door at eleven, sharp, on Saturday morning, she answered immediately. Obviously, she had been waiting for him. She did not invite him inside but she came out to join him on the step.

  She was wearing a flannel shirt, hiking boots, and blue jeans. Her hair was tied in a ponytail. Her expression was grim.

  “You look like you’re ready for a hike,” Craig said, a tinge of concern in his voice.

  “Don’t worry. It won’t be strenuous,” she replied. “At least not for you.” She tried to speak with a light, confident tone and almost succeeded, but he could hear a quaver of fear pushing through. “We’re going to be a little bit country and a little bit city today.”

  He waved the envelopes and said, “When do I open Number One?”

  “We’ll take my car, but you have to drive.” She locked her front door, then handed him her keys. She looked wistfully at them as he took them from her.

  He was miffed that she had not answered his question directly, but told himself that this was her show and if this was how she wanted to play it, then that was up to her.

  She waited by the passenger door of her five-year-old Subaru Impreza.

  Ever the gentleman, he unlocked it, held it open, waited until she slid in, then closed it carefully.

  As soon as he slipped into the driver’s seat, he saw a note taped to the steering wheel. It read, “Please open the first envelope.” That was vintage Leslie. Everything was planned to the last detail. No need for him to ask questions.

  He removed the note from the steering wheel and dropped it onto the console, then tore the first envelope open.

  Leslie was staring straight ahead, her resolve etched into her face, not wanting to see his reaction to her instructions.

  He read silently:

  Drive out along Highway Five to County Road Three. Stop by the road in an area that looks swampy and let me out. I will return with a willow switch. Take me to the Princess Motel at 1554 Washington Street and wait while I check in. When we get to t
he room, I will strip, gag myself (for the sake of the other guests), bend over, and wait for you to stripe my ass with six of your best. Do not hold anything back when you apply the strokes. This is punishment. I expect to be punished. Give me plenty of time to feel each stroke and to anticipate the next.

  If this is the last envelope, let me ungag myself. If not, open the next envelope after my caning.

  Craig folded the paper and put it back in the envelope. Leslie’s day was going to start with a bang. If this was the least of her punishments, he wondered how bad they were going to get before they were finished.

  * * *

  Leslie spoke not a word during the half hour drive into the country but her intermittent ragged breaths betrayed her fear.

  When he stopped the car, she opened the glove compartment and pulled out a classic black-handled Buck 119 hunting knife. It was brand new. She left the sheath and carried the knife with the blade bare. It felt heavy in her hand – a masculine, no-nonsense, tool for a serious hunter.

  When she left the gravel shoulder, her boots squelched through the sopping swamp grass. She wondered if she should have specified less practical clothing for this exercise – a formal dress with high heels, maybe or no clothing at all – but it was too late to change the rules. Once the envelopes were sealed, nothing could be changed. Besides, foolish clothing or their lack would have only distracted her from the main event – finding a proper switch. She wanted to find one that would hurt. Really hurt. If she received anything less than his most severe caning, it would not be her fault. It was her duty to make sure that she put the right cane into his hands. She wondered if Craig could swing a cane hard enough to break her skin. She expected him to try.

  She walked for some distance before she found a clump of willows and began searching for a nice straight branch with at least a three-foot-long, straight span. Not too thick, a thinner cane would sting more but might cut the skin too easily; but not too thin, either, because it had to bruise the muscle deeply enough. She thought that something about the thickness of her index finger would be about right.

  After sorting through the thicket for a few minutes, she found a suitable candidate. It was a little thinner than she wanted, but not too thin. She started cutting it loose.

  Cutting through the limb took longer than she expected. A strong man might have done it in a single stroke of the knife, but she had to whittle away one chip at a time. And she had to cut all the way through the branch; she was worried that it might split if she tried to break it off and then she would have to look for another.

  Once it was free, she had to cut the other end off, as well. That took another equally long time because the cane was almost the same diameter at the distal end as at the base. When she was finished, she gave it a couple of experimental swings. It felt substantial in her hand, but was thin enough to be nice and flexible. As she listened to it whistle through the air, she knew that Craig would soon be administering a severe punishment with it. Her ass cheeks twitched in fear of the beating that she had prescribed.

  She had specified only six strokes, but, if Craig laid into her the way that she had instructed, that would be enough to cause considerable suffering. Already she wished that she had won all games and avoided any penalty.

  She would soon be wishing that wish a lot harder.

  If wishes were fishes, she’d be star kissed.

  * * *

  Despite its name, the Princess Motel offered less than royal accommodations. But it was not grungy, either. It was about the best you could get for under a hundred bucks in this part of town.

  The clerk was a middle-aged man with a slight paunch and a baldpate. He wore no wedding ring but he had a henpecked air about him.

  When she asked to pay cash for one night in advance, he said that he would need to take an impression of her credit card for her security. She could have asked him how it would make her secure to give her credit information to a total stranger but she had other concerns on her mind so she let it pass. She quietly handed her MasterCard to him, let him swipe it, and received a freshly programmed electronic key card in return.

  She carried the suitcase from the trunk of her car to the room. It was heavy and the contents tended to shift and clank as she walked. The willow switch did not fit inside, so she had to carry that openly in her other hand.

  She tried not to think too much about what was coming.

  In the room, she pulled off her boots and left them by the door, then set the suitcase on the bed and opened it. Craig did not bother trying to peer inside – he knew that he would be familiar with the contents by the end of the day. Rather, he sat in the easy chair and watched her prepare herself for her caning.

  He was surprised when her first action was to pull a pocketknife from her jeans and carefully peel the bark from the cane. The slick white wood looked even more wicked when it was bare. She used a Kleenex from the bathroom to wipe the moisture from the butt end so that he would have a firm grip, but left the rest of the cane wet. She handed it to him and said, “I expect nothing less than your best effort.” It was the first words that she had spoken since telling him that he would be her chauffeur for the day.

  He nodded.

  She unbuttoned the flannel shirt and slipped it from her torso, revealing a plain white bra, and then pulled her jeans down to reveal plain cotton panties. They came off along with her socks. When she was naked but for the bra, she looked down at it for a few seconds, debating. Strictly speaking, there was no need to bare her breasts to get her ass caned. But, after a moment’s contemplation, she decided that she would look a little silly wearing a bra when her more intimate parts were available for inspection. She slipped it off and added it to the pile of her other clothes. She was struck by the morbid thought that Craig might be able to hit her hard enough to make her unrestrained boobs bounce.

  As soon as she was naked, she pulled a penis gag from the suitcase. She needed something that would keep her quieter than a ball gag; this would fill her mouth much better. She was under no illusions that it could keep her totally silent, but she hoped that it would keep her quiet enough that any guests in the neighboring rooms would not feel duty-bound to call the police. She took a deep breath, understanding that it would be some time before her mouth was empty again, then opened wide, inserted the gag, and buckled it behind her head.

  She pulled the second easy chair into position next to the bed, then pulled the low coffee table to the other end of the room, giving Craig as much room as he would need to swing the cane in a full arc.

  Without further ado, she pressed her feet together, bent as far as she could over the back of the chair, grabbed the seat cushion, and waited for the first stroke.

  Craig stood up slowly, enjoying the view of her taut buttocks perfectly presented for administration of the cane. They were a perfect womanly size: neither small nor large; slightly padded with a layer of subcutaneous fat, but not dimpled with cellulite.

  Her round cheeks quivered with anticipation of the suffering that was about to be visited upon them.

  He swished the cane through the air three times to limber his wrist and forearm. Her buttocks twitched reflexively as she heard each practice swish, not certain which one would land on her ass. Then, without warning, he set his stance, raised his arm and brought the switch down across her backside as hard as he could. The arc was long and the cane whistled loudly before crashing into her flesh with an explosive impact.

  There was a second of silence and then she began to howl through the gag like a baying hound. Her feet never left the ground, but her legs danced in place, making her ass cheeks bounce as though they had a life of their own.

  A single stripe of white was painted across the middle of both cheeks, perfectly symmetrical and parallel to the floor. As he watched, it slowly turned pink, then dark red. The skin was not broken, but she would be wearing an angry welt for some days to come.

  He waited until her howls subsided to whimpers, then commented, cruelly, �
��I bet you wish you were a better backgammon player, now, don’t you?”

  She could not respond through the gag.

  People talk about a person’s ass feeling like it was on fire, but that description utterly failed to describe the pain that Leslie felt. Sitting on a hot barbeque could not possibly hurt as much as this single stripe. She guessed that he must have cut through her flesh all the way to the bone and tried to feel if there was wet blood flowing down her legs.

  She did not know if she could stand five more strokes. After feeling this, she realized that she should have instructed that she be bound before the beating because she feared that she would not have the strength of will to maintain her position until the sixth stroke was delivered. Sometimes being bound is a mercy.

  She had almost written “a dozen of his best” in the instructions, but had changed her mind at the last minute because this was supposed to be the minimum penalty for losing a single game and should not be too severe. Some minimum penalty. She knew that men had more upper body strength than women, but she never would have guessed that Craig was strong enough to do this much damage. This single stroke was a complete torture all on its own.

  He delivered another mighty blow to her ass.

  The cane whistled then cut into her with a sharp report.

  She shrieked through the gag and grabbed the cushion on the chair so tightly that she drove the blood from her knuckles, making them as white as the second stripe that popped across her ass.

  Craig waited while the blood flowed back into the strip of severely damaged flesh and the stripe developed into a second thick, red welt. This stripe fell a little above the first one and angled down to almost meet it at the far end. He would have preferred to be able to lay down a series of perfectly parallel stripes, but did not have the skill. By the time he was finished, he would be more experienced, but then it would be too late to correct his earlier work.