The Lady Gammons Herself Good

by Ashley B. D. Zacharias

“I’ve been playing a lot of backgammon on the Internet lately and it’s become boring.” Leslie raised an eyebrow. “The time has come to spice it up a little. Again.”

“So you want me to spot you again?” Craig asked.

“If you wouldn’t mind,” Leslie replied, feeling herself blush as she remembered the last time he had helped her “spice up the game.” She lowered her gaze.

“I don’t mind.” He sipped his coffee, then added, “Same setup as last time?”

“I’ve changed the rules a little. To make it more interesting for myself, you see.”

“So what are your new rules?”

“I have six envelopes with numbers on them.” She waved a handful of manila envelopes at him. “At the start, I hold numbers one, two, and three; you hold four, five, and six. I’m going to ignore the matches and play as though I’m playing a series of single game of backgammon–”

“On the Internet,” Craig injected.

“Yes, on the Internet, just like last time.”

“Okay,” he smiled. “I just want to make sure that you don’t plan on playing against me this time.”

She laughed nervously, “Don’t worry. I want something more challenging than that.”

“If you’re going to insult me, then I might just start hoping that you lose all the games.”

“Don’t be cruel.” she said, a mocking tone in her voice.

“Okay. So you’re playing backgammon. What then?”

“Just like last time, these envelopes contain penalties. I start with three penalties and I’m playing to get rid of them. Every time I win, I get rid of an envelope by giving it to you.”

“And when you lose, I bet you take an envelope back from me.”

“Exactly. Every time I win, my penalty gets easier; every time I lose, my penalty gets worse.”

“And this whole thing ends when either you get stuck with all the envelopes or you get rid of them all, right?”

“Or when I chicken out. I can stop playing any time I want. So let’s say I get down to only one envelope. I might decide to stop playing then, when I have only a little penalty to pay rather than risking losing and getting some envelopes back. That’s the fun part. After each game, I have to decide if I want to take what’s coming to me right then, or if I want to take a chance of improving my lot by risking getting myself in deeper.”

“So how bad are these penalties?” Craig asked, looking at the stack.

Leslie looked down at them, then back up and said, “I don’t want to have to serve any of them, not even Number One. But the thought of having to work through all of them, right down to Number Six terrifies me. The only way that I could force myself to stuff that envelope was because I knew that I could stop at Number Five.”

“So is it the usual schedule? That you play today and, if you lose, you pay your penalty next weekend?”

“If you’re free next Saturday, I’d like that to be the designated penalty day.”

“I can do that.”

“Then let’s play some backgammon.” Leslie handed Craig the bottom three envelopes, then led him to her computer.

“What about the doubling cube?”

“That would double it to two envelopes, of course,” she replied, already distracted by her first roll.

The first game was close. Her anonymous opponent played adequately, though not brilliantly. The dice favored him slightly, but not enough to tip the scale against her superior strategy. He had five men left on his One and Two Points when she cleared her inner table. She smiled at Craig and said, “That gives me a little breathing room,” as she handed him Envelope Three, leaving only two envelopes in front of her.

The next game went well until they began bearing off. She had a substantial lead and doubled her opponent, expecting to force him to resign. Instead, he accepted the double. “Great,” she commented. “Now we’re playing for two envelopes and I’ve only got two left. I’m going to beat him and that will clear my penalty completely.”

She was trying to sound happy, but Craig heard a note of disappointment in her voice. Maybe she didn’t want to pay even one of the penalties, but he knew that she wanted more excitement than simply winning two games outright and ending the drama.

She needn’t have worried, though; the gods of the random number generator were feeling evil today. Her opponent rolled double sixes and double fours in succession, reversing her lead. A few minutes later, she had to ask Craig for Envelopes Three and Four. He noticed that her voice had an unmistakable tone of dismay. It seemed that the fourth envelope was the cutoff point. She didn’t seem to mind the first three envelopes nearly as much as the fourth. Whatever was in there would push her beyond some limit.

Now she was playing for keeps.

Her opponent was happy to have won the game and quit without finishing the match. That was typical of a lot of the lesser players who styled themselves as “experts” but never wanted to push their luck.

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 having to pay all six penalties.

“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 one 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 as 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 permanently injured 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.

It was predictable. Leslie was stable as a rock in most aspects of her life and career, but when it came to self-punishment, she would take the gamble every time. Craig knew that.

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 kept them in my possession.” she said in a watery voice. “Can you be here at eleven o’clock on Saturday?”

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

When Craig knocked on Leslie’s door at eleven, sharp, on Saturday morning, she did not invite him inside but she came out immediately. She was wearing a flannel shirt, hiking boots, and blue jeans. Her hair was tied in a pony tail. 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.

He was miffed that she had not answered his question directly, but told himself that this was her show and if this is 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, 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 cane. Take me to the Princess Motel at 1554 Washington Street and wait while I check in. When we get to the 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 cane. This is punishment. I expect to be punished. Give me plenty of time to feel each stroke and anticipate the next.

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

Craig folded the paper and put it back in the envelope. Leslie’s day was going to start with a bang. He wondered how bad it was going to get before it was over.

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 in her hand. It felt heavy – 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 span. Not too thick, a thinner cane would sting more, 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.

It took longer than expected to cut through the stick. A strong man might have done it in a single stroke of the knife, but she had to whittle one chip away 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 preordained.

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.

Although the Princess Motel offered less than royal accommodations, it was not too grungy, either – about the best you could get for under a hundred bucks.

The clerk was a middle-aged man with a slight paunch and a bald pate. She noted that he wore no wedding ring but did have 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 the card to him, let him swipe it, and received a freshly-programmed electronic key card.

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 pocket knife 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 chauffer 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. Naked but for the bra, she looked down at it for a few seconds, debating. Strictly speaking, there was no need to take it off to get her ass caned. But, after a moment’s contemplation, she decided that she would look a little silly wearing only a bra. 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 a little quieter than a ball gag and this would fill her mouth much better. She was under no illusions that this could keep her totally silent, but hoped that it would keep her quiet enough that any guests in the neighboring rooms would not be impelled 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.

They quivered with anticipation of the pain that was to come.

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 if one would land on her. 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, “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 stripe. She guessed that he must have cut through her skin 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 courage to maintain her position to the end. She had almost written “a dozen of his best” in the instructions, but had changed her mind at the last minute because she had decided that 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 as the second stripe that popped white across her ass.

Craig waited while the stripe developed into a 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 it would be too late to correct his earlier work.

He was anxious to see if he could do better so, before her shrieks had subsided noticeably, he raised the cane and let fly with the third stroke.

Her shriek flew up a full octave. She sounded like the world’s worst opera soprano singing a one note aria. She pushed herself half upright, her hands leaving the seat cushion, releasing the tension in her buttocks to try to reduce the pain.

“Hey! Get back down there! You’re only half done!” he snapped and she obediently forced her head back toward the seat cushion.

This stripe fell below the first and was parallel to the second, the trio forming a tilted, elongated “Z” that was not quite closed at the corners.

He waited until her shrieks subsided to ragged sobbing. That took a long time – two or three minutes – but he did not mind. He was in no hurry.

This time he gave her lots of warning. “Ready?”

She nodded her head.

“Brace yourself. This will be the worst one yet.”

She whimpered through the gag and gripped the cushion at tightly as she could.

He flicked the switch through the air a couple of times, making it whistle.

She whined in fear.

He raised the cane high and paused, watching her big muscles twitch and quiver, then brought the cane down hard in at an angle that cut across all three previous stripes.

Laying in the cane at this angle reduced the force of his stroke slightly but that small mercy was overbalanced by the agony of the blow overlaying previously damaged flesh at three points; he was rewarded with a whole new chorus of screams. It sounded like three different women were screaming behind the one gag. Leslie had developed a whole new talent as a screaming virtuoso.

He hoped that the neighboring rooms were unoccupied, or if they were, that the occupants would think that a TV was blaring, because this gag was proving less effective with every stroke. “Hey, Leslie,” he hissed, “try to keep the noise down a little, okay? You don’t want to have to explain yourself to the management, do you?”

She heard him because her screams lapsed into sobs immediately. She was almost out of her mind with the pain; it filled her whole world. But, through the fog of agony, she knew that, as bad as this physical pain was, the humiliation of having to explain her situation to a stranger would be far more agonizing for her.

She gasped for air. The pain was literally taking her breath away. On top of that, she had to draw air around the gag because her nose was clogging up from her crying; but it was difficult to breathe around the gag because her mouth was filled with saliva and she was drooling copiously on the seat cushion. On top of all that, her diaphragm was compressed across the back of the seat. She feared that she might suffocate. Her misery was complete. She took as deep breath as possible and blew out her nose. She was beyond caring about the chair.

Two more, she told herself. Only two more. I can stand that. I can. I will. I have no choice.

She never considered standing up, removing the gag, and telling Craig that she had changed her mind. Leslie could no more chicken out than she could sprout wings and fly. It was not her nature.

Then she heard Craig say, “Let’s try this. Let’s see if you can take this next stroke without a sound. No howling or screaming or crying. Not even a whimper. Let’s see you take this one in complete silence.”

Leslie shuddered. This was not the deal. There was nothing in the instructions about being silent.

“What do you say? Will you give me silence?”

She nodded slowly. He was doing her a hell of a favor. She owed him at least this much in return.

“Quiet now,” he cautioned, and let fly.

When she heard the dreaded whistle, she clenched her ass tight and bit the gag as hard as she could.

Her backside instantly blossomed in a new explosion of agony. She stopped breathing. If no air flowed through her throat, then she would make no sound. But she could only hold her breath for seconds before she was gasping for air again.

She could feel her legs dancing in place uncontrollably, her body trying to escape the pain even though her mind would not let her run away.

As she concentrated on not screaming, not whimpering, not even sobbing, one thought intruded. One more. Only one more stroke to endure. Suffer only one more and she could stand up. One more and she could walk away. Just one more.

Craig waited until she settled down again. He was not going to deliver his last stroke to a moving target.

Eventually her legs stopped dancing and she bent her torso down as far as possible to present, one last time, the perfect target for his brutality. But her ass kept quivering violently, vibrating with tension. It was not something that she was doing voluntarily; he suspected that she did not even know that it was happening. It was just a reflexive response of her flesh to the damage that it was sustaining.

The five stripes were rather haphazardly placed, different lengths crossing at odd angles. It was hardly artistry, but he decided that it was safer to make sure that they all fell close to the center of her buttocks. If he struck too high, he risked damaging her back; too low and would hurt her legs. The ass was the safest target, especially for blows this hard.

As he watched her waiting submissively for her punishment to end – he glanced at the five remaining envelopes that he had brought from the car and revised his thought: she was waiting for the first part of a full day’s punishment to end. While waiting, he reviewed his technique the way a violinist in a master class would review his bowing. What would happen if he put more wrist action into his stroke? He could probably add considerably more speed to the cane just before it landed.

He would try that with his last stroke. He owed it to her to make this stroke a good one. She had asked for punishment and he had agreed to deliver to the best of his ability.

So he delivered a full measure.

With the extra snap of the wrist, the last stroke was the most vicious of the set. The flexible willow switch struck so hard that it wrapped itself partway around her right buttock, leaving the longest stripe of the day. As the white mark bloomed to angry burgundy, small beads of scarlet blood welled up in the five places that this stripe crossed earlier stripes.

The beaten woman’s screams sounded inhuman through the gag. She howled like a banshee, a long, shrill ululation that could call the dead from their graves and summon the hounds of hell.

She tried to rise, but could not stand straight – the muscles in her buttocks were too damaged, the pain too intense. Her hands fluttered at her sides, wanting to caress her burning nether parts, but fearing to touch anything lest she elicit a new wave of agony. She staggered two steps to the bed and fell upon it, curling into a loose foetal position next to the open suitcase and let her howls fade to deep, racking sobs.

Craig looked at the poor woman’s mouth still wrapped around the end of the penis gag, her jaw opened as far open as she could extend it to allow breath to enter and sobs to leave; then looked down at the injury that he had inflicted on her buttocks – a half dozen deep red furrows, each flanked by stiff ridges of swollen flesh. He worried that he had beaten her too enthusiastically. He should never have laid his whole strength into his strokes. He should have pretended. Playacted the part, but pulled his punches. Let her feel duly punished without giving her the full British boarding school treatment.

He sat beside her and stroked her head tenderly, then said, softly, “I’m sorry.”

She snapped around to look at him, her red, tearful eyes suddenly flashing in anger. She jerked away from him, pushed herself off the bed despite the new pain that she was inflicting on herself, and hobbled over to the desk. Instead of simply unbuckling the gag and pulling it from her mouth to speak to him, she grabbed the pen and a pad that was emblazoned with the Princess Hotel tiara logo, and scrawled in a fast, barely legible script, “Don’t you dare feel sorry for me! And don’t you dare feel a second of regret for doing what I instructed! Don’t you dare!!!”

She hobbled back to the bed, thrust the note into his hands with an angry glare, then fell back into her foetal position and began sobbing anew, letting her pain fill her completely, washing away all thoughts, all regrets.

Leslie stayed on the bed for almost half an hour. Craig brought a box of Kleenex from the bathroom and put it beside the bed so that she could wipe her nose delicately and frequently. She looked grateful for that small mercy.

After her sobs had subsided to whimpers and then her whimpers gave way to moans and finally her moans fell to silence, she gingerly rose from the bed, gag still in her mouth, drool flowing freely, and shuffled over to the bathroom to gaze long and hard over her shoulder at the damage that had been inflicted. The striping looked as bad as it felt, but she was relieved to see that there was little blood, apart from the few dots that had been left by the final stroke. She had feared that she had been cut to the bone; her ass felt like it should be hanging in shreds.

Gingerly, she let her fingertips explore the welts, ever so gently. The mortified flesh felt stiff and unnatural. She wondered if the strokes would leave permanent scars. She hoped not because, though she was not fond of her ass, judging it too big and fat, she did not want it made any more unsightly. As it stood now, she wouldn’t be appearing in a high-cut bathing suit any time soon. If she had known two hours ago what she knew now, she would have cut a smaller switch. Much smaller.

She turned from the mirror and saw Craig watching her. She held up two fingers, signaling that she was ready for the second envelope. Her day had begun in earnest. It would be a long time before it came to an end.

Craig ripped open the second envelope and read:

You get to relax. I do not need you help to administer this punishment to myself. The only caution is that you must not assist me in any way, no matter how much I might beg or plead though the gag and no matter how long I take to build up enough courage to free myself. You may only release me if something has gone terribly wrong and you have already called an ambulance.

P.S. I hope you like baldies.

He did not like the sound of that at all. Was she planning something that could result in a trip to the emergency ward? He hoped that she was joking about that. Funny stuff. Ha, ha. Her self-destructive streak scared him stiff. Sometimes literally.

When he looked up from the letter, he saw that Leslie was already rummaging through her suitcase. She pulled out a pair of handcuffs, a long strip of cloth, a big white jar, and a handful of little plastic spatulas. His mystification deepened when she began warming the jar in the microwave oven. He realized that she must have checked that the rooms included microwave ovens before she chose this motel. Leslie was a thorough planner. Craig had to give her credit for that. He suspected that she kept a whole drawer full of “to do” lists next to her bed.

While the jar warmed up, she kept herself busy by forcing the one corner of the six foot long, two inch wide strip of cloth through the hole in a standard handcuff key and tying it securely in place with a proper reef knot. When the microwave dinged, she extracted the jar, fiddled around with a little plastic spatula, poking at its contents, then re-heated the jar for another quarter minute. After repeating this ritual twice more, she was satisfied by its consistency.

She gathered the jar, spatulas, and cloth strip (with the key firmly attached), laid them out on the coffee table, and then pulled a chair close. Finally, she fetched a bath towel from the bathroom and laid it across the seat of the chair. She groaned in misery through the gag when she lowered herself gingerly onto the chair. Her beaten ass must still hurt like hell.

When she raised her legs, spread them across the arms of the chair, and grabbed the jar, Craig understood what evil thing she was about to do to herself.

She scooped a liberal daub of warm brownish wax out of the jar and spread it in a small patch through the hair at the base of her pubic triangle, then grabbed the strip of muslin cloth an inch from the end of the handcuff key and embedded it firmly into the wax. Over the next couple of minutes, she applied the wax to her entire triangle of pubic hair, embedding the muslin strip as she went. Rather than a single big patch of wax, she had been careful to create a dozen small patches, each separate from the other, each with a different part of the muslin strip embedded. She would not be able to remove the whole strip with a single quick yank, but would have to pull it off piece by piece.

When she was finished, she minced back to the bed, trailing a three foot length of muslin. To Craig, it looked like her pussy had sprouted a tail. Without giving herself time to think about what she was doing, she snapped the handcuffs about her wrists behind her back.

Now she would not be able to reach the key that dangled so enticingly close below her pubic patch until she had removed the entire muslin strip starting at the free end – a process that would entail stripping off all her pubic hair, one painful patch at a time.

She had a full, thick mat of hair – obviously she had not shaved in some time in preparation for this event – and every one of those well-rooted hairs was embedded in the hard, cold wax.

Leslie walked over and looked at herself in the full length mirror, assessing the predicament that she had devised for herself, hoping that she could find a flaw in her plan. If she could find an easy way out at this point, she would take it. Her penalty was to put herself in this predicament and get herself back out. It did not specify a particular method of escape. She moved her handcuffed wrists as far to one side as she could and then back to the other side. She satisfied herself that she could not get to the wax directly. Her only option was to pull the rip cord.

She squatted so that the cloth was lying on the floor, then took a half dozen little steps forward until she could grab it with her hands. She tried pulling. It was no use. She could not get her hands far enough between her legs to pull down on the cloth, and she could not slide it between her legs. As soon as she pulled, it was forced up into her cunt where there was too much friction to move it. Trying to pull it across her clit and through her labia would cause more pain there than the ripping of her hair from her flesh.

She sighed in frustration through her gag.

Her next attempt had slightly better success. She dropped the strip to the floor, squatted down, put the ball of her foot firmly on the end, and then stood up. Or, at least she tried to stand up. When she was half way up, the cloth drew taut and began pulling her hair. She tried to force herself up further, screaming through the gag, but could not do it. She was pulling too slowly. The idea was good, this execution was lacking. She squatted again, took a few deep breaths, and then tried to snap to her feet in one motion. By focusing on her effort to straighten her legs and ignoring her crotch, she managed to rip out the first chunk of hair – a patch about an inch square. Craig heard the sound of the hairs ripping out of her pussy scalp. She screamed through the gag in pain and shock, then looked down to see the hairy chunk of wax hanging on the muslin strip. The newly bared patch of skin on her mons pubis glowed bright pink.

Waxing is normally done when the wax is still soft enough to peel the hairs away in a running line – painful enough at the best of times. By now, though, Leslie’s wax patches were solid and she was pulling whole chunks of hair out at a time – a considerably more painful process.

She repeated this action several more times: squat, step, stand, scream through the gag, then look down in dismay at how many patches were still left to go. And the process was not made any easier by the preceding caning – every time she had to squat and pull the major muscles in her ass taut across her pelvic bones, she groaned in agony. It was a slow, cruel waxing to be sure.

She was panting around the gag with the accumulated pain before she was less than half finished. Then she got another brilliant idea. She hobbled over to the corner of the bed, dragging several feet of cloth dotted with little wax scalps across the carpet, squatted down, and working blind with her hands behind her back, managed to tie the free end to the bed leg. When she was finished, she stood up, bent over as far as she could so that the cloth was clear of her crotch when it was extended back toward the bed, then took two running steps. Before the second step landed, the cloth strip pulled taut and successfully yanked three tufts of hair from her crotch before killing her momentum. She screamed, first in pain, then in triumph at the amount of naked crotch that was freshly revealed.

Three more times she backed up, took a run, and screamed through the gag. The final pull that cleared the hair from her pussy lips was almost anticlimactic.

Now the muslin strip lay free of her, stretched across the room, studded with a dozen patches of hairy wax, leaving the bright steel handcuff key lying on the floor within reach. It took some effort to pick up the key because she wanted to avoid resting her damaged ass on the dirty carpet. She first carried the towel from the chair and laid it on the carpet, then sat on that to reach the key. After a couple of fumbles, she managed to get the key into the handcuff and release herself.

She could not speak around the penis gag that still filled her mouth, but the look of triumph in her eye said, “That’s how self-bondage is done,” as clearly as if she had been able to articulate the words.

She massaged her bald pubic mound for a minute, trying to rub the pain away.

She reached back behind her neck and unbuckled the penis gag. She sighed when the saliva soaked stub slipped from her mouth. She flexed her jaw a couple of times, but remained silent. She could talk now, but she had nothing that she wanted to say.

Craig did not feel that it was his place to break the silence, so he sat in his chair and watched to see what she would do next.

She held up three fingers.

Craig tore open the next envelope and read:

The third penalty is not pain, but humiliation. You may think that this penalty will hurt me less than the others, but rest assured that I’m am going to hate performing it more than either of the first two penalties. You should know that the keys to the locks are inside my house so I’ll be wearing this contraption for the remainder of my penalty day. If this is the last envelope, that will last until I walk home from here. If not, then I’ll be double stuffed for even longer. I hope you enjoy my performance. Be assured that I will not.

When he looked up from the envelope, Leslie was pulling a plastic bag from her suitcase. She laid it on the bed, next to a big black dildo that she had already unpacked. Finally, she laid out a black leather harness and two small padlocks.

She could not meet his eyes – she kept her gaze cast down toward the floor as she moved the suitcase from the bed to the coffee table.

She bent over the bed, thrusting her ass toward Craig, and spread her legs wide, exposing her puckered asshole for his enjoyment. There was a butt plug, previously lubricated, in the plastic sandwich bag. Taking it out, she reached between her legs and began working it into her asshole. It was big enough to stretch a virgin asshole to its limit, an inch and a quarter in diameter at the widest point and four inches long. It flared wide at the end so that it could not accidentally slip inside her.

Though the plug had been liberally lubed with Astroglide, her asshole had not; she had to keep working it in and out of her hole to get enough lube inside as she stretched herself open. Every time she pulled the plug back out, Craig could see that her asshole was gaping open a little wider. Occassionally, she wiped the sides of the plug against the edges of her hole to keep putting more lube into herself.

Finally, with a sharp grunt, she managed to work the widest part past her sphincter. If humiliation was her goal, Craig decided to give her a little extra of what she craved. He stood up and walked over so that he could watch closely while her distended asshole slowly contracted around the plug, which was almost an inch in diameter at its base.

He stepped back when Leslie slowly stood erect, adjusting to the feel of the big plug that her filled anus. She walked cautiously into the bathroom, taking small, wide steps, and returned with another bath towel. She laid it on the bed, laid on her back, bent her knees, and spread her legs wide to give him an unobstructed view of her cunt.

The anal plug had been pre-lubricated; the dildo was not. To avoid tearing, she would have to stimulate herself to get enough natural lubrication to let her work the full eight inchs inside. She was already somewhat wet the morning’s play, but it takes more than a moderate amount of lubrication to make that much silicone slick enough to slide that far inside a woman.

She parted her inner lips with the fingers of her left hand and pushed the end of the artificial cock against her pink inner flesh. It barely penetrated and, when she pulled it away, had only a small ring of shiny fluid around the tip of the head. She worked it around a few more times, making more of the head slippery so that she could work more inside.

Once the head was fully enclosed, she began vibrating it manually, in and out, and around in little circles. She panted – quick, sharp, shallow breaths – and thrust her hips back and forth to meet the dildo as though she were humping a real man.

As the dildo was working in and out, slowly, it was sliding a little deeper with every thrust, her cunt getting wetter and wetter as it dilated to accommodate the inch and three-quarter diameter. The silicone cock was ridged with prominent veins that caressed and stimulated her lips as they flicked in and out.

Craig, watching the show, felt as hard as the dildo and, despite his devotion to his wife, wished it was his real cock that she was working into her sweet pussy instead of just anonymous molded silicone.

It took a few minutes for her to accommodate the entire shaft but eventually she managed to take it right to the base. The dildo was not intended to be inserted the full length into a woman. When it was, the head pressed hard against Leslie’s cervix, compressing it deep inside her and causing considerable discomfort.

When she was finished, her face was ruddy pink, a perfect match to the inside of her blood-engorged cunt, which he could no longer see because it was completely blocked from view by the oversized dildo that she had forced into herself. Craig did not know how much of her vivid facial color resulted from her exertion, how much from sexual stimulation, and how much from humiliation, but suspected that she felt plenty of the latter. Leslie was a naturally shy person and he did not doubt that it had required a terrible force of will to let him watch her fuck herself with a dildo. He felt honored that she had let him observe her most intimate act as closely as he wished.

She moved her hand down to check that the anal plug was still in place, that she had not dislodged it while working the dildo. Just to be sure, she gave it a strong push before she wriggled slowly off the bed and pushed herself erect, holding her legs wide, the stubby black ends of the two foreign objects peeking out from the folds in her pussy and ass.

She turned back to face the bed and picked up the black leather harness. First she buckled the belt tight about her waist, then buckled a strap tight between her legs. That strap had a wide hourglass shape in the middle that completely covered the ends of the dildo and anal plug. Without hesitation, she clicked one padlock through the buckle at the waist and the other through the buckle on her lower belly.

Now, there was no way that she could remove the dildo and anal plug until she removed the belt; there was no way that she could remove the belt until she removed the padlocks; and, according to her instructions, she had no way to unlock the padlocks until she returned home.

She would remain double fucked until her punishment day was over.

She put her legs together as best she could – the edges of the strap pressed against the inside of her upper thighs – and carefully paced the length of the room, feeling the sensations of the double stuffing and testing the limits of her movement. The dildo pressing hard against her cervix made her feel crampy. As long as she moved carefully, she could walk without hurting herself too much, but the tight straps about her waist and between her legs made every step an unique study in discomfort.

She slowly moved the easy chair and coffee table to the wall, clearing the middle of the room, then removed a small cardboard box from the suitcase and set it on the table. She laid a package of heavy-duty fourteen-inch cable ties next to it. Finally, she pulled the metal frame chair from the desk to the middle of the room and sat down, ever so cautiously because she was not only sitting on her badly beaten ass, she was also sitting on the end of the dildo and anal plug.

For the first time since he opened the third envelope, Leslie met his eyes.

She held up four fingers. Her hand was shaking like a poplar leaf.

Something bad was coming.

Craig opened the envelope. His eyes grew wide as he read:

Secure my arms and legs to the chair. Use lots of cable ties so that you can secure me firmly without cutting off my circulation. Blindfold me. Put on a pair of rubber gloves. Use the small bottle of alcohol and cotton wipes to sterilize my right nipple. Sterilize one of the safety pins with the alcohol. Push the pin through my nipple right at the base. Safety pins are not nearly as sharp as hypodermic needles, so it will take some effort. Take your time and work it through the nipple as slowly as you wish. Ignore any crying or pleading. This is the fourth penalty, so it should be severe. Be careful not to prick yourself. When you have finished, slide one end of the short chain onto the pin, clip the pin closed, then use the pliers to crush the safety catch so that the pin and chain can only be removed by cutting it off. By now, you must be hungry. Go out and have yourself a nice, leisurely meal. I’m not hungry at all, so just leave me in the chair, anticipating your return. When you feel in the mood, come back and pierce my left nipple the same way. Don’t forget to sterilize me and the pin. And don’t forget to slide the other end of the chain onto the pin before crimping it closed. Give me a few minutes to settle down before you remove the blindfold and cut the cable ties.

If this is the last envelope, finish up as instructed in the paragraph below, otherwise, stop here.

There were two more envelopes to go, so he did not bother reading the remainder of the instructions on this sheet.

He looked at his friend, sitting submissively in her chair, her arms lying on the arms of the chair and her calves already pressed against the chair legs, anticipating and dreading the pain to come. Her face twitched slightly with fear.

He looked into the box and saw two regular-sized safety pins – the old-fashioned kind with metal heads that completely enclose the tip – the kind that mothers use to pin diapers closed.

As well, there was a foot of chain. It was larger than he had expected, the steel links were about a quarter inch in width. It felt heavy in his hand.

Very well. If she wanted pain, he would deliver it in spades.

He strapped her forearms to the arms of the chair using a dozen cable ties, then strapped her calves against the chair legs in the same fashion. She could bend her torso forward and move it from side to side, but that was all. Presumably, she could also bounce up and down in the seat a couple of inches but she was not about to do that with the dildo crammed against her cervix.

There was a black fabric blindfold in the cardboard box. She closed her eyes as he slipped the elastic around her head. It fit snugly; she could see nothing.

She listened to his movements – quiet footsteps walking away, the rustle of a pair of latex gloves slipping first onto one of his hands, then the other. She held her breath to listen more closely and heard the cap scrape a little as it was removed from the alcohol bottle. There was a gurgle, then nothing. She stained to hear something, some clue about what he was doing, but he had fallen silent.

Suddenly she felt cold wet on her nipple. It contracted to a hard button. One hand lifted and held her breast while the other swabbed the entire nipple and areola with alcohol. She could smell it, sharp and irritating in her nostrils.

Nothing happened for a long minute. Was that to give the alcohol a chance to evaporate or merely to give her a little more time to suffer the anticipation of the pain to come?

Then she felt his latex encased hand grab her nipple and stretch it out. She gripped the arms of the chair as tightly as she could. She was not gagged, but did not dare scream for fear that someone would call the police. This was the time to be brave. She had never felt less brave in her life.

The needle pricked the base of her nipple. Just a little, but it hurt more than she expected. Then it began to hurt a lot more. Her friend was developing into a true sadist. He pushed and twisted the pin through her ever so slowly, working the point back and forth, up and down, parting her flesh millimeter by millimeter.

She gritted her teeth and felt her eyes well up with a flood of fresh tears.

Surely he must be almost through by now, the agony was lasting so long. She whimpered like a newborn kitten. The nipple is replete with sensitive nerves and he was hitting every one. The most sensitive of all was on the surface of the nipple and, as he slowly pushed through those nerve clusters from the back, she wanted to scream her lungs out. But she did not; her will was strong. Under Craig’s insistent pressure, her sensitive skin was tented by the blunt point further and further until it finally parted, allowing the bloody steel tip to poke through. But that was not the end of her suffering. He kept pushing the pin through until the punctured nipple was centered in length of the pin. Not only is a safety pin relatively blunt, but the shaft is unpolished so the course texture made her damaged nerve ends dance in pain as it tugged and plucked at them. Her blood left small streaks along the length of the roughly milled steel as it passed through her flesh.

Finally, she felt him slide an end link of the small chain over the pin, then heard him clip the point into the safety catch with a little snick. The weight of the chain pulled the pin painfully in the fresh piercing when he dropped it. A few moments later, her nipple was tugged far more painfully by pin in the newly pierced hole as Craig lifted and twisted it so that he could fit the safety catch between the jaws of the pliers and crush it closed around the point.

She heard the clunk of the pliers being place back on the table; then heard him say, “I worked up an appetite, all right. Sure I can’t bring anything back for you?”

She shook her head. Her stomach was twisted into knots. This penalty was not finished – she had a wait for an unspecified time before the second nipple would be brutally pierced – and she had to serve two more penalties – the worst ones yet. She could not have forced herself to eat even if she had wanted to.

The door slammed, leaving her sitting, blindfolded, feeling her nipple throb with every heartbeat. And every throb was echoed by a larger throbbing ache in her well-beaten ass.

She sat in misery. Time stretches long when a person is in pain and has no distractions. She knew this, but, as her suffering stretched longer and longer, she began to wonder if Craig had decided to go home and spend the rest of the afternoon cooking a gourmet meal for himself.

As agonizing minute after minute crept past, she felt her dread growing. The first piercing had hurt more and lasted for longer than she had expected. She was caught in a double bind – on one hand, she did not want to feel that same pain in her other nipple anytime soon; on the other, she wanted her punishment to end as quickly as possible.

She strained to hear him come back. She could hear cars rushing down the road constantly. Twice she heard cars turn into the parking lot in front of the motel, but neither stopped in front of her room. She wondered if it were growing dark outside. Craig had not opened the fifth envelope yet so he did not know that she had to complete her penalties during business hours. What would happen if he left her here for too long? Strictly following the rules in the envelopes, she would have to leave herself plugged and pierced until her penalties were complete; and, if businesses were closed today, she would not be able to complete her punishment until tomorrow.

She did not want that – that was more penalty than she had bargained for. She wondered if a woman could die of toxic shock from keeping a silicone dildo inside her for too many hours. She strained harder to hear him coming, but heard nothing.

Until she heard the scrape of a key in the door.

For the first time, a new thought struck her. What if this was not Craig? She had not heard her car return to the space in front of the room. What if this were a maid? Or, even worse, the bald, pot-bellied manager from the front desk. Maybe she had not been quiet enough. Maybe someone had heard her whimpering and had called the manager to ask him to investigate.

Surely not. Surely if it were the manager, he would knock first and ask if everything were all right. That was standard practice, wasn’t it? For safety’s sake, she had arranged not to be gagged while Craig was absent. If someone called through the door to her, she could yell back that she was all right and send them away.

The door clicked closed. She could see nothing through the blindfold, but sensed that she was no longer alone. She wanted to ask if the person in the room with her were Craig, but remained silent. She would know soon enough and if it were not, she could do little about it now.

She quivered with tension in her bonds and strained to hear, but the person was being ever so quiet.

When she felt cold wet cotton suddenly soak her left nipple with alcohol, she squealed in shock. Once again, she smelled the sharp odor and felt her entire areola and nipple being drenched, a sure sign that new pain was coming soon, driving her fear to a new peak.

When she felt her nipple grabbed and pulled taut, she gripped the arms of the chair with all her might and gritted her teeth. It was all she could do to keep from screaming as the pin began slowly working into her sensitive flesh. It worked and hurt and worked and hurt and she strained against her bonds and lost all awareness of her other pierced nipple and beaten ass and stuffed orifices. Her left nipple became her whole world; nothing else mattered in her entire life.

She had not choice except to endure, so endure she did while Craig stretched her ordeal out for as long as he could manage.

But, eventually, everything comes to an end, this piercing included. The point finally pressed though to the other side, Craig finally threaded the pin through the end link in the small chain, and finally crimped the safety pin closed. The chain was not overly heavy, but weighed enough to pull the safety pins down so that her nipples were slightly twisted under the weight. He left Leslie bound to the chair for long enough to feel the fresh throbbing in her left nipple fade somewhat. That was hardly a relief because it left her feeling the ache in her butt again. The points of pain on her body were accumulating and becoming harder to tolerate with every new punishment.

As she sat, she found the plugs strapped into her ass and cunt grew to bother her more than either her sore nipples or her bruised ass. It was not so much that they hurt as they simply felt wrong. The more she thought about them, the more she wanted them out of her body.

But there was no way for her to remove them until she got home again and that was going to take some time yet.

As soon as Craig snipped her free of the cable ties with the pair of diagonal cutters that had been included in the cardboard box, she pulled her blindfold off and looked down at her chest. She saw her two nipples were pierced by safety pins and connected by a foot of steel chain that sagged between her tits, exactly as she expected.

She held up five fingers.

Craig tore the fifth envelope open.

The instructions in Envelope Five read:

Time for a fresh round of humiliation. Lock my hiking clothes in the trunk of my car and wait while I get dressed in my slut clothes. Penalty Five is not complete until I test drive a new car. All you have to do is to wait until I get back.

If this is the last penalty, then follow the instructions below to finish up. If it is not, then you should open Envelope Six as soon as I am out of sight.

Once again, Craig did not bother reading the remainder of the sheet. He was too concerned with the situation that Leslie had put him in. This was the first time that she had done anything in public; the first time that she had involved strangers. If the wrong people got mixed into her games, it would be dangerous for both of them. He did not like the thought of having to protect her from some violent lunatic and risk getting beaten or worse. He had his own family to think about.

He wanted nothing more than to call the whole penalty off right here and now. But, as much as he wanted to, he knew that it would be a waste of breath. There was nothing in this envelope that required action on his part. If he backed out, she would merely carry on without any protection.

He looked at her silently, fury in his eyes.

She looked back, and knew what he was thinking. She had known what he would think when she had typed up the instructions two weeks earlier. “You don’t have to do it, you know. You’ve been terrific so far. Done more than I dared hope. You can just leave. I’ll be walking home regardless. Drive yourself back to my house, get into your own car and drive home. Throw my keys into the juniper bush by the front window. I’ll find them and let myself in when I get back.”

Of course, he could not do that. He shook his head.

“Okay, then.” she paused. “Look, if anything goes wrong, don’t get involved. Just call the cops and let them sort things out. Tell them that you were driving along, recognized me and noticed that I was in trouble. I’ll back up your story. It’ll be cool.”

Craig gathered her clothes together and carried them outside and deposited them in the trunk of her car. In for a penny, in for a pound. That was the ancient wisdom. He was staying until the end, no matter how bitter.

When he came back, Leslie was pulling a dress from the suitcase. It was a hot pink sleeveless double knit dress with a scoop neck. It did not look slutty until she pulled it over her head and he saw how it settled around her body. The neck scooped low enough to show ample cleavage, almost revealing her areoles. The safety pins and chain connecting them made some odd bumps but they were tiny; her nipples were swollen by the raw piercings and forced out enough to tent the material so that the extra bumps on the sides were not unnoticeable unless you knew to look for them. In the same way, the locks on the waist and crotch straps made slight bumps of their own, but the straps had been tightened enough that they were drawn deeply into her flesh pulling the locks away from the material. Again, you had to know what you were looking at to tell that the bumps were caused by padlocks rather than just folds from badly-fitted underwear.

The hem was short, rising almost to her crotch. Nothing untoward would show as long as she did not try to raise her hands above her head or bend over to touch her toes. When she sat, though, she revealed a lovely long length of naked thigh, all the way up to half the curve of her butt.

Leslie slipped a pair of matching pink patent leather high heels on her feet. After she strapped them about her ankles, she took a tube of Gorilla glue and fastened the entire length of the free ends of the straps. These shoes were not coming off until she cut through the leather. The heels were high, more than two and a half inches, but not ridiculous; the toes were sharply pointed. They would be comfortable enough if she stood for only a little while, but painful if she had to walk more than a short distance in them.

She had already told him that she planned to walk home. That was a good five miles from the motel; considerably more than a short distance. And her instructions talked about test driving a new car. The nearest car dealership was almost a mile in the wrong direction. It appeared that she intended to walk at least seven miles in these pretty little shoes. They would be instruments of torture worthy of the Inquisition by the time she made it back.

She extracted a makeup kit from her suitcase and carried it into the bathroom. When she came out a few minutes later, she had painted her lips crimson and her lids sea green to match the color of her eyes. A liberal application of eye liner and mascara made them look as big as saucers.

Craig felt himself getting hard just looking at her. The feeling in a man’s groin provided the true definition of “slut clothes.”

Finally, she pulled a regular-sized padlock from her suitcase and set it on the table. The hasp was open. “I’m going shopping for a car. You should open the last envelope before I return.”

He watched her pull a tiny clutch purse, pink to match her shoes, from the suitcase and exit the motel room. As soon as the door was closed, he opened the curtains and watched her mince across the parking lot. He could tell that she was doing her best to walk normally, but she was taking one slow, careful step after another. The objects stuffed into her cunt and asshole, the strap pulled tight between her legs, the pain in her ass and tits, and the high heels made every step a unique exercise in discomfort. At this rate, it would take her at least a half hour to walk the mile down Washington Street to the Lexus dealer. According to his rough calculations, she would have between three and four hours of walking before she made it back home, in addition to whatever time she spent completing the last penalty. By the time she finished, she would be in utter agony. These were six envelopes of punishment indeed.

And that presumed that she did not encounter any problems. He hoped that she could get a test drive at the nearest dealership. If not, she would have to walk another half mile to the Toyota dealer on the other side of the street. A woman alone, dressed as she was would not likely strike a salesman as a serious shopper. Sexual stereotyping was still thriving in the automobile retail industry and she had handicapped herself with her outfit. She might have difficulty finding anyone who would let her test drive any kind of vehicle.

Craig was not going to let her do this without his discreet supervision. As soon as she was out of sight, he was going to lock the motel room and follow in her car. As long as she was on the street, he was going to keep her in sight – an easy task when she was making such slow, painful progress on foot.

First, though, he tore open the final envelope.

The last instructions said:

Do not return my keys until I come back to the motel and show you semen smeared on my face. When I can show that I have collected a semen sample from a car salesman, then you can separate the two halves of my keychain and use the last padlock to lock my house key to the chain between my nipples. You get to drive home to pick up your car. I get to walk. You can slip my car keys through the mail slot on my front door.

Craig guessed that car salesmen would not likely to be eager to let a slutty-looking single woman test drive a car and he had been right. In Leslie’s case, though, he had not anticipated her resourcefulness. She knew that she would face rampant sexism, but figured that she could make that work in her favor. It would only require a modicum of additional self-debasement.

First, though, she had to get herself as far as the dealership. As she walked down the sidewalk, every step jostled the dildo against her cervix deep in her cunt and made her flinch. Though it was a light fabric, the wool dress slid back and forth against her nipples with each step and irritated them more and more; and it rubbed across her stripped ass with equal force. Every time her legs parted, a cool breeze blew up the short hem and across her hairless cunt, a constant reminder that her modesty was at risk of a false move – not that she was about to bend over and touch her toes with the dildo and anal plug shifting around inside her, but even sitting carelessly would be a problem. Not that there was any place where she could sit and rest in this suburban wasteland. And, of course, her toes slid down and forward inside the pointed shoes with every step, squeezing and pinching them with ever increasing pain. Leslie would feel no instant of joy until she made it back home and was able to free herself. She had far to go before that happened, figuratively as well as literally.

She was most concerned about the last requirement that she had imposed on herself – that she get some kind of facial. She had never before engaged in casual sex and dreaded, more than any beating or painful restraint, having to proposition a strange man – especially when only her mouth and hands were available for his use, her cunt and asshole being otherwise occupied. Though this was not accidental – she was less likely to catch a sexually transmitted disease from oral sex than from the regular kind – the necessity of using her mouth posed its own problem. She was not a complete novice, but she was far from an expert fellatrix. The truth was that she had engaged in oral foreplay with men on a few occasions, but had never sucked a man off to completion. She was not entirely certain how to do it and only prayed that she would receive divine inspiration when the chips were down. Or, to be more accurate, when she had gone down on some stranger.

This last penalty was going to be an enormous challenge – the one that she feared might be too much for her – which was why she had tried so hard to avoid it. It would have been so much easier if she had stopped playing after five envelopes and had only had to talk a salesman into giving her a test drive without a blow job included.

Her mouth was dry with fear.

When she finally made it to the Lexus dealer, she forced herself to walk confidently onto the lot, gritting her teeth against the assorted aches in her feet and legs that threatened to hobble her and turn her bold stride into a pathetic limp.

She walked directly into the show room and began peering at the cars. Being the late Saturday afternoon, the place was busy – a small squad of salespeople were attending to a flock of other customers – mostly families with small children. She dared not bend over too far to look into windows and study the vehicle interiors for fear that she would flash her crotch harness. Looking around, her new worst fear was that, if she bent over even a little, some kindergarten-aged girl would start pointing at the black leather digging into her private parts and shouting, “What’s that, Mommy? What’s that lady wearing?” She stayed as erect as possible and did no more than read the specification sheets glued to the windows.

She was unconcerned with price or features; her only concern was finding the vehicle that would best allow her to fellate a man in the front seat without getting her dildo and ass plug jammed any more deeply into her body. If that were the primary goal of every wife who walked onto a car lot with her husband, there would be far fewer sports cars sold; and far fewer divorces pending.

A nice SUV would do fine. The RX seemed the best for easy, slutty sex. She imagined an advertising campaign based on that premise and managed to smile through her pain and fear.

After looking at every display model in the showroom, she looked around for a salesman. As soon as she looked up, a middle-aged woman in a business suit smiled and clicked across the marble floor toward her. “Can I help you find something?” A small gold plaque pinned across her left tit identified her as “Marion.” If she had been Marion, Leslie would have made sure that the pin on the plaque pierced more than the material on her blazer.

Leslie cursed her luck. She wasn’t going to be able to milk any jism from this broad. And she wouldn’t earn her house keys back with cunt juice; the instructions had clearly said “semen.” She replied, “I’m just looking at the moment.”

“Okay. Let me know if you have any questions. My name is Marion.”

“Okay. Thank-you, Marion.”

She spent another few minutes looking at the cars, waiting for a salesman of the masculine persuasion to free himself from his other clients. First man free will get a real sales bonus. No sale, but a real bonus.

But, before any of the salesmen in sight were available, two additional men entered the showroom, laughing and sipping coffee, coming back from a break. One, the younger, was handsome enough in a rough-hewn fashion. His face, though scarred from a long-ago struggle with acne, was slender with high cheekbones and a strong jaw. His frame looked strong and lean inside his well-tailored suit. The other man was middle-aged, thirty pounds overweight, his paunch straining the buttons on his too-tight shirt. His face was jowly and had been shaved rather haphazardly. He tried unsuccessfully to hide his bald pate with a comb over of straggly gray hair that was held in place with an excess of mousse. He wore no wedding ring, but looked married.

Given a choice, Leslie reasoned that the least attractive man would be the most receptive of her attention; and be the least likely to be infected with a STD. She hoped that he was too faithful to his wife to frequent prostitutes, but not so faithful that he would turn down a free blow job.

She approached the two, working hard not to wince at her various aches and pains, and addressed the middle-aged man, ignoring the other. “Excuse me, sir, but I was wondering if you could tell me a little about the RX.”

The two men looked at each other, then appraised her slowly. The younger man slapped the older on the shoulder and said, “Catch you later, Bill.” He sauntered off to find his own hot prospect. She smiled to herself, knowing that he would never find a prospect as hot as her.

“What would you like to know?” Bill asked, his voice not expressing any degree of enthusiasm. He doubted that she was really in the market for a forty-thousand-dollar car; fifty if he could talk her into all the options. And he could talk her into them; Bill excelled at pushing the options.

“My boyfriend sent me down here to buy a car for myself and some of the other girls. He said we’ve earned a good one. It’s kind of a business vehicle, and I think this one would be real nice.”

“Your boyfriend?” Bill asked.

“Yes, sir.”

“What kind of business are you in, miss?”

“I guess you’d call it personal services.”

“I see,” he glanced around. He dared not ask her to describe her “personal services” in any detail for fear that some innocent child would overhear the wrong answer and his parents storm into the manager’s office. Or worse, leave the lot without buying a car. But her evasive comment did convince him that his initial impression; that she was serious about purchasing something; and that she had the money to do so. Probably in cash. He was warming to his newest client already. Leslie had neatly leveraged his chauvinism to her advantage. Her ability to assess people’s weaknesses and exploit them was why she was so successful in her legitimate professional life. “So what do you like best about the RX?”

“It’s nice and roomy, isn’t it?”

“It certainly is.” Bill proceeded to give Leslie his standard spiel about all the special features of the RX, explaining the options packages in detail. He went to extra lengths to describe the comfort features that, in his estimation, would most appeal to a working woman.

Leslie stood there for more than ten minutes, nodding with her sweetest smile pasted on her face, enduring the agony in her feet, the dildo jammed against her cervix, the overstretched sphincter, and the sharp bite in her recently pierced nipples. She wanted nothing more than to move to the next stage of her punishment as soon as possible, putting her another step closer to the blessed keys that were waiting on her kitchen table. But she had to make him think that he had almost sold her on the vehicle before he would take her on a test drive. There were too many other customers in the show room for him to waste time on the road with a casual looker, no matter how good she looked.

Finally, he wound to the end of his over-practiced speech and delivered his standard last line, “So what will it take to put you in the driver’s seat of this fine vehicle?”

“This sounds like the perfect car for us. Just lovely. But it’s kind of big. I’m worried that it might be a little hard to drive. You know, difficult to park and all.” She shifted her weight to her other foot to ease the pressure on her poor toes, but the dildo shifted deep inside her and brought on a sudden cramp. She could not help but wince.

Bill interpreted the pained expression on her face as concern about driving an SUV. “Don’t worry about that, darling. It might be an SUV, but it handles better than the average mid-size cars built by other companies. This is a Lexus, after all. I give you my personal guarantee that, when you drive it, you’ll think you’re dreaming.”

“I’d like to see that for myself.” Her asshole had been stretched so wide for so long that her only dream was popping the plug out and letting it relax back to its normal petite size.

“Well, certainly. I wouldn’t expect you to buy a car before you’ve given it a proper workout. If you just let me borrow your driver’s license, I’ll arrange a vehicle for you to test drive as soon as possible.”

“Thank-you. I would appreciate that.” He could not possibly guess how much she would appreciate a test drive. She opened her little pink purse and drew out her driver’s license. That was the only reason that she had brought a purse and that was the only thing inside. She had brought no money or credit cards just to ensure that she had no way to chicken out and avoid the long walk home by calling a cab.

“If you’d like to take a seat,” he gestured to a black fake-leather and chrome bench by the back wall, “I’ll have a test vehicle brought around. It may take a few minutes, so make yourself comfortable.”

There were already a couple of other people sitting on the bench waiting for their own test drives, but there was ample room left for her.

It did not matter in the least. All the room on all the benches in the world would be insufficient to make her comfortable. Being able to take her weight off her feet would only mean that she would have to rest her weight on her bruised and aching butt, as well as forcing the dildo and anal plug deeper into the most sensitive parts of her anatomy.

As she was taking her seat, she pulled the hem of the short dress down as far as possible, stretching the top tight against her burning nipples, and pressed her knees hard together, the better to hide the apparatus locked through her crotch and across her bald mons pubis.

She ignored the other people on the bench and they pretended to ignore her. But she was acutely aware that the men on either side were staring at her long, naked legs with hooded eyes. She toyed with the idea of short-circuiting her penalty by giving one of these men a blow job – they were obviously interested – and then leaving directly. But she dared not. If Craig were watching the lot and did not see her in a car with a salesman, then she would not have satisfied the penalty and he could keep her locked out of her house until she returned tomorrow and accomplished exactly what her instructions had specified. And there was no way she would get a test drive if she had one of these men’s jism smeared across her face. Her only option was to wait until she could satisfy the penalty properly.

The dealership was busy, everyone wanted to try out one of the vehicles, so she had to wait on the bench for more than three-quarters of an hour before her salesman returned. It was almost five thirty – she had been suffering continuously for six hours – when he finally came back, saying, “I’m sorry that took so long, but we’re really hopping today. Everyone wants to drive a Lexus, you know. If you’ll follow me, I’ll show you to your new ride.”

His pathetic attempt to sound cool fell cold on Leslie’s ears. She forced herself to stand back up on her pink stilettos and hobble after him out to the lot.

The salesman insisted on holding the car door open for her, a phony display of false gallantry that gave him his best opportunity to ogle her tits and legs. When she had to step up into the driver’s seat, she knew that her hem hiked up past her crotch, giving the man a clear view of black leather and hairless skin. Undoubtedly, he did not understand that he was seeing a chastity belt over double-stuffed womanhood; instead, he undoubtedly thought that she was wearing some kind of kinky leather thong. She hoped that the sight made him horny because she wanted him to be the horniest salesman in the city.

As soon as he entered the car on the passenger side, he launched into his pre-test-drive spiel – another tedious ten minute lecture about all the RX’s comfort features and options. He was largely repeating information that he had already given her in the show room, but this time he could point to the actual levers and knobs. For the most part, he delivered this spiel to her tits instead of her face. While he talked, he stared at the erect nipples pressing hard against the thin pink double knit wool, not realizing that they were being pushed out by the safety pins piercing them at their base. His eyes delved deep into the dark fleshy crevasse where her widely-separated braless breasts pushed the deep-scooped neckline away from her sternum – she wondered if he could catch a silver glint of stainless steel chain down there. He studied the choreography of her tits as they thrust and flexed against the fabric of her bodice with every breath she took. During the entire spiel, his eyes never met hers once.

No one had ogled her tits so openly for so long since she had been trapped in high school history class in the seat next to Dirty Jimmy Gibson for an entire semester, but, now, Leslie did not care so much. Every part of her was aching – aching in pain, aching to get this humiliation over with, aching to get home again. All she could do was to wait for him to wind up his speech and hand over the keys. That was her entire focus. Getting those keys in her hand.

It seemed like hours before he finally said, “So, let’s go for a spin.” He finally raised his gaze to her face and dangled a key on a string in front of her.

“Thank-you,” she said, taking the proffered key and sliding it into the ignition. The warm engine turned over easily and caught instantly. When she reached up to adjust the rear view mirror, she felt his eyes ogling her tits from a new perspective. Outside the car, it had been from the front, during his spiel, from the top, and now he was treated to a side view where her tit was almost popping out of the sleeveless hole. Every angle gave him new joy.

She followed his instructions as he directed her off the lot, down the street, and through the suburbs. He kept talking about the soft ride but she kept feeling the dildo bang against her the top of her cunt and the anal plug bounce in her ass every time the car hit the slightest bump. She had never before been so aware of the impact of road conditions on an automobile’s suspension. After a few minutes, she took the initiative. “I want to try parking,” she said, and turned into an industrial park.

“Of course,” he replied, but there was a note of uncertainty in his voice. No one had ever taken a test vehicle down this particular road before and he was not happy about any deviation from his comfortable routine.

She ignored him. She was in the driver’s seat so she was in control. She was always in control. In her own perverse way, she had been in control all day long. That was the point – to exert control even over herself in ways that she would not like. Self abuse is the ultimate expression of the true control freak.

She parked at the far side of an empty parking lot. It was late Saturday afternoon; there were no other cars in sight.

As soon as she was parked, she killed the engine, turned to the salesman, and said, “I want to give you a blow job.” She felt her cheeks burn hot with shame as the words passed her lips.

“What?” The man’s eyes flew wide open.

She reached across and gave his prick a gentle caress through his pants. “Right here, right now, I want to take your dick out of your pants and lick and suck you until you come all over my face.”

“You’re out of your mind,” he stuttered. “No. No way. Take me back right now.”

It was not the reaction that she had expected.

“It’s okay. It’ll feel great and no one will ever know. It’s just a private thing between you and me. I want to take you into my mouth. My nice, soft, sloppy-wet mouth.” She could feel that he was hard. Why was he not pulling his dick out of his pants in eager enthusiasm?

“You’ll get the leather seats all wet. This is a new car.”

“I’ll be careful.”

“No. I don’t do this. I don’t pay for sex.”

“Have I asked you for money? I don’t want your money. I want to make you happy. That’s all.”

“Do you think I’ll give you some kind of special deal? Is that it? You think that I’ll take thousands of dollars off the price of this car if you give me oral sex?”

“No. I’m not asking you for anything. I’m offering myself for nothing. I just want to make you feel good.” She gave him another little squeeze through the gabardine.

“I’m married.”

“That’s okay. I’m not asking you to divorce your wife. This will help your marriage. You never have to see me again and you’ll have a new fantasy to think about when you are with her. How often does she give you nice blow jobs?”

“That’s none of your business.”

She fumbled for his zipper. “Please. Just let me do this and then we can go our separate ways. Please.”

“No.”

“I’m begging you.” She felt her eyes welling up with tears of pain and frustration. “I need this. Please let me do it for you.” She could not believe that she had to beg a middle-aged, bald, pot-bellied, badly-groomed car salesman to let her suck his dick. This was more humiliation than she had bargained for. “I really want you. Really.”

A sly look came into the man’s eyes. “Really?”

“God, yes. More than you can guess.”

“Well, then, maybe we can work out a deal, here.” He was sounding like a car salesman again.

“Whatever you want.” She suddenly feared that he would ask her for money. How much would a gigolo expect a woman to pay for sex? Any amount was too much because her purse was empty. If she promised him money, she would have to stiff him. There was a certain poetic justice to that idea of stiffing a stiffie.

But he wasn’t going to let her off cheaply. “If I let you give me a blow job–”

“And come on my face.”

“And come on your face, then you have to buy this car.”

“Buy this car?”

“Not exactly this car. A fully loaded Lexus RX in the color of your choice.”

“Buy a car?” she was stunned.

“That’s right. That’s what I do. I sell cars. And this is what you do. You give blow jobs. So you do what you do and let me do what I do. You give me a blow job and I sell you a car. That’s fair.”

That’s a fifty-thousand dollar blow job, she thought. That’s a damned expensive piece of cock. But every part of her was aching, from her feet to her ass to her nipples. “Okay, I’ll do it,” she said. “Let me get you out,” and she reached for his belt.

“Not so fast. We have to go back to the lot and sign the papers first.”

“Blow job first, papers later.” She feared that he might not hold up his end of the deal once she had signed a sales agreement. Even in the depths of agony, she knew to keep her wits about her. She wasn’t born yesterday. And she was not about to trust a car salesman.

He looked at her face, long and hard. She looked back with equal determination, the steel in her gaze clearly communicating that he was not going to sell a car until after he received his blow job. Finally, he shrugged and said, “Hell. Why not? But not here. You do it back in the office after I’ve prepared the paperwork.”

She saw a sly glint in his eye despite the bland tone in his voice. He planned some kind of treachery; she would have to keep her wits about her. Which was difficult after so many hours of torture.

She pulled out of the parking space and drove directly back to the car lot. He did not bother telling her any more about the car; she said that she was going to purchase, so as far he was concerned, he had closed the sale. Saying anything more would be a waste of breath.

She suffered miserably for another half hour, sitting in a chair in front of his desk, answering questions while he filled out form after form. She had to choose the color of the vehicle – silver – and the options – all of them – and he had to check the spelling of her name against her driver’s license before returning it to her.

Finally, there was nothing left to be done but scrawl her signature in the space provided. “Time to give you your pleasure,” was her only response, ignoring the pen he offered. “Where should we do it?” They were in an open cubicle, visible to everyone who walked by. If she had to, she would crawl under his desk but she hoped that he had a more private venue in mind. Business hours were ending, but there were still a couple of customers negotiating deals as well as all the salesmen roaming around, tidying up after a full day’s work. Sucking this man off would be humiliating enough without having to provide a show for his colleagues. “The lady’s washroom, perhaps?”

“Let’s go to the private meeting room.” She could tell by the gleam in his eye that some kind of treachery was drawing closer, but she still did not know what he might be plotting. He stood and led her down a short hallway to a small room that contained a table and four chairs. When he stood aside to let her walked through the door first, her back was turned to him for a few moments. He gestured to one of the other salesman, waving frantically and pointing to the manager’s office next door.

The other salesman nodded, understanding his signal.

Inside the room, Leslie was getting straight to business. As soon as he stepped inside, she pushed the table against the closed door, the better to discourage people from barging in, then pulled one of the chairs into the empty space that she had cleared. “Come on, mister,” she beckoned, then, when he was moving too slowly, pulled him into place by his belt. As soon as he was standing in front of the chair, she dropped to her knees and unbuckled his belt. It took a minute of fumbling to work the buckle and he had to unbutton his waistband by himself because his belly put too much pressure on the buttons for her to manage without his assistance.

When his pants and boxers were pulled down to his knees, she pushed him firmly into the chair, then bent her head over his half-erect cock, shoving her nose into his thin nest of graying pubic hair, and began working him, first licking him fully erect, then wrapping her lips around his head and sucking greedily. He tasted stale, but not as bad as she had feared.

As she worked on him, she stared at his thin, gray hair and thought ruefully that he now sported more than she did on her newly waxed crotch.

She had to work on him for only a minute before his hips began bucking against the chair, thrusting his cock deeper into her mouth. Once fully aroused, he grabbed her head by her hair on both sides of her scalp so that she could no longer pull back and began fucking her mouth in earnest. She wanted to gag when he hit the back of her throat, but she carried on like a trooper.

As she choked under his abuse, she would bet a considerable amount of money that the man’s wife never volunteered for this kind of treatment. Blow jobs would be a rare treat for this guy.

Kneeling with her ass stuck out over her heels, her head bouncing around from his increasingly vigorous strokes, the anal plug was stretching her in new, more uncomfortable ways while the dildo was ramming itself hard and painfully against her deepest recesses. Her pain was increasing exponentially. Mercifully, once he began fucking her hard, he came quickly.

As soon as she felt his cock begin to pulse, she yanked her head back out of his hands, losing a few hairs, and waited for him to spray her face.

There was no spray. He dribbled.

She had to get his dribble on her face to earn the keys to her house back from Craig. She howled in frustration, scooped the drops of thick cum from the head of his prick with her finger and smeared it across her cheeks herself. That task was done. Score one more triumph for Leslie.

But he wasn’t done; he was still pumping out more dribble. He grabbed the back of her head and pushed her mouth down over his cock again. “Lick me clean, whore. Finish the deal.”

She licked him clean and swallowed the remainder of his cum. A deal was a deal.

When she looked up at him, he grinned down at her and said, “Now I’m sure that you’re going to sign those papers and buy that car. You know why?”

“Why?” she asked, having every intention of welching on the deal now that she had what she needed. As far as she was concerned, she’d given him more than enough charity already.

“Because your performance has been watched and recorded in living color.” He laughed. “There’s a camera hidden in that air vent behind you and, by now, the manager’s office is full of salesmen watching your every move.” He waved and she heard a muffled chorus of cheers echoing through the wall.

Another woman’s first reaction would be to twist around and try to find the camera, but Leslie felt such a wave of humiliation that she merely dropped her head in shame.

The salesman looked at the top of her head and laughed at her embarrassment. “I guarantee that, as soon as those guys saw what was happening, they popped a disk in the recorder. If you don’t sign those papers then I’ll be uploading a little movie onto the Internet and the whole world will be seeing how well you suck cock, Miss Leslie Holden. And I also know that you’re not a real whore at all. You don’t suck cock well enough to earn a living at it. Besides, my assistant ran a quick check on you while we were preparing the paperwork. You don’t want all your friends looking at you as the latest Internet porn star.”

She looked up at him with tears in her eyes, mostly from accumulated pain and exhaustion but also with the knowledge that her punishment was far from over. “You moron,” she replied. “I’m not in trouble. You are. If they didn’t put a disk in until they saw me dropping your pants then my face isn’t on that recording. I’ve had my back to the camera throughout. But your face is there. If you don’t get to that disk and destroy it before your buddies hide it from you, then copies will be circulating around this office for years and years.” Bill’s face fell in shock when he realized the truth of his situation. She pressed her point, “It’ll only be a matter of time until your wife sees it, either by accident or more likely sent by a malicious coworker. That Marion looks like just the bitch to do you in at the first opportunity. If your wife doesn’t throw you out immediately, then she’ll be damn sure to make the rest of your life a living hell. Run, Bill, run. Run fast or you’ll be suffering for a long, long time. Have a miserable life, asshole.”

Bill missed her last words. He was still trying to drag his pants over his hips when he threw the table aside and trotted out the door.

Alone for the first time in two hours, Leslie pulled herself back to her aching feet, re-adjusted her dress, scooped up her purse, and limped out the door. As she walked through the showroom, she heard a tremendous brouhaha roaring out of the manager’s office. Furniture was being thrown against walls. Personally, she didn’t care who ended up with Bill’s home made porn video because she didn’t care who saw the back of her head. She was only happy to finally be leaving with a nice smear of Bill’s cum drying on her cheek.

And she didn’t mind missing her chance to buy a Lexus SUV, either. She preferred small cars.

The mile-long limp back to the motel hurt even worse than the limp to the car lot; made worse by the knowledge that her punishment was going to continue for some time yet.

Craig was waiting patiently inside the motel room. She knew that he was a good friend, but she would never know how good. He had not only followed her to and from the car lot, but had been following her around during the test drive as well, just making sure that, if she needed help, he would be close by to give it to her.

As soon as she was inside the motel room with him, she turned her cheek and said, “Right there. That crusty spot is a salesman’s cum.” She smiled an evil smile. “You can smell it if you like. Just to be sure.”

“No thanks,” Craig smiled grimly. “I’m happy to take your word for it. Can I drive you home now?”

It took all her will power to force herself to say “No thanks.” Rules were rules and the instructions in Craig’s hand did not include a ride home. After all she had been through, she was not going to wimp out now. She grabbed her dress at the hem and raised it above her breasts, revealing the chain that linked her nipples. “The house key goes here, remember? You can drop my car keys through my mail slot when you pick up your car.” Her keys were on the kind of double key ring that snapped together, the house key on one side and the car keys on the other.

Craig did not reply, but true to the instructions, separated the two halves of Leslie’s key chain, threaded the hasp of the padlock through the ring that held her house key and then padlocked it to the chain that hung between her boobs. The padlock was not small and not light. When he gently lowered it to hang from the chain, its weight dragged the safety pins through her nipples to the ends, distorting the raw piercings painfully.

“Ouch,” Leslie said with conviction. “That smarts.”

“You won’t take the key off the split ring until you get home?” Craig asked curiously.

She laughed bitterly. “Not even then. The split ring is soldered closed. I have to use the key from where it is until I can get inside and unlock the padlock.”

“You’ve though of everything.”

She lowered the dress gingerly back over her tortured nipples and bruised ass, being careful not to jostle the lock that was hanging on her. “I hope so.” She reached up, grabbed the lock through the double knit, and raised it slightly to relieve the pressure from her nipples. “I’ll be hanging on to this all the way home. If it bounces, it’s heavy enough to tear the piercing out. Better to have a tired arm than a ripped nipple.”

“Five miles is a long way.”

“If I leave now, I should be getting home about the time it gets dark. I’ll be safe enough on these streets. I can’t thank you enough for all the time you’ve spent helping me today.”

“You’re welcome.” Craig wondered if she would be still thanking him after she found what he had put inside her house.

Without further comment, they left the motel, him driving her car and she hobbling down the street. The room was rented for the night. She would drive back and get her things before checkout time in the morning.

For Leslie, the walk home was tedious agony. Every step hurt her feet. Every step hurt her cunt and asshole. Every step dragged the wool double knit across her ass and tits. The fabric was soft to the casual touch but, after five miles of abrasion, felt like sandpaper against her tender, and tenderized, parts. And every time her attention wandered, her hand that was holding the padlock through the dress relaxed and let the lock tug sharply on her wounded nipples. That snapped her back to reality. There was no excitement in this, just labored punishment.

By the time she reached her front door, the tears that were streaming down her cheeks had washed the salesman’s cum all the way down to the base of her neck. She wanted a shower so badly it hurt.

Her car was back in her driveway; Craig’s was gone. Undoubtedly he had been home snuggling with his wife for over three hours already.

But her ordeal was not over, even yet. Her plan contained a final humiliation. The key for her front door was inside her dress. She could not remove the objects from inside her nor the pins from her nipples until she could unlock the door and get to the keys and wire cutters that she had left on her dining room table. The only way that she could get the key into the lock on her front door was to hike her dress up to her shoulders, leaving herself naked from her armpits down. She dared not exhibit herself to her neighbors – she had to live here – so she could not get into her house until was too dark for her to be seen. At this time of year, the sun set at about nine, but she had programmed her front porch lights to stay on until ten. And she had installed fresh, bright, hundred watt bulbs in the fixtures on each side of the door. If she tried to let herself in early, in the blaze of two hundred watts, people would see her from a block away. The final instruction in every envelope from Four to Six had included locking her house key to her tits. She had known when she was playing the backgammon games that, if she quit when she was stuck with Envelope Four and her nipples were going to be pinned, then her ordeal could not end until ten o’clock at night, a full eleven hours after it began.

She spent the next hour and a half sitting on her back step. She could only hope that none of her neighbors were peeking over the back fence because the dress was too short to cover much below her waist when she sat with her knees halfway up to her chin. She spent the time just sitting and weeping, her tears flowing from pain, frustration, exhaustion, humiliation, and no small amount of relief that the end was in sight. It was only a matter of waiting now.

When she turned around, she could see the clock on the microwave through her kitchen window. When it showed nine-fifty-five, she limped painfully around to the front of her house and stood on the front porch until the lights clicked off.

With a final scan of her street to make sure that none of her neighbors were out walking their dogs, staring out of their windows, or driving home, she knelt on the sill of her front door, hiked her dress up over her breasts, and pulled the key toward the lock. The chain was short, she had to stretch her nipples out to get the key into the hole, making her piercings burn with fresh pain, but, by positioning herself as close as possible and stretching her nipples far enough, supporting the padlock with her free hand, she managed to insert the key and turn it without tearing a safety pin out. When the lock clicked open, she gasped with relief, withdrew the key ever so carefully – this was no time to rush and make a mistake – dropped her dress, opened the door, stumbled across the threshold on her knees, and pushed the door shut behind her.

She groaned with relief. She would be free of all her torture devices in a few minutes. Keeping a hand on the padlock to support it, she pulled herself back to her feet using the front door knob, and then, before going to the dining room to get the keys and wire clippers, she limped into the kitchen, grabbed the shears from the counter, and cut the straps on the pink high heels. It was surprisingly difficult to cut through the thin leather, but the shears were up to the task. The shoes fell to the floor, one by one. She felt such relief when she was allowed to stretch her poor bruised toes again that she began to cry anew.

She walked barefoot into the dining room, closed the curtains, then turned on the lights.

She had left wire clippers on the table next to the padlock keys, but when she looked at the table she saw that they were missing and there was another envelope in their place. The words, “Envelope Seven” were typed on the front. What the hell was this? She had never made a seventh envelope. If she had, it would have contained a terrible punishment.

With shaking hands, she tore it open.

The paper inside read:

Dear Leslie:

Surely you remember that you were gammoned in the last game, losing two points. You deserved two envelopes, but, at that time, I had only one to give to you, Envelope Six. This one, Envelope Seven, is the last penalty that you earned for yourself by accepting the gammon. If you do not want to accept your final penalty, that is your prerogative, but you lost the points, so I think you deserve a full measure of punishment.

This is your final punishment.

You may not remove the safety pins or the chain connecting them from your nipples for three months. Clean the pins with alcohol to keep from getting an infection and move them from side to side daily to ensure that your flesh does not grow attached to them. With proper care, your piercings will be permanent by the end of three months. At that time, you can replace the pins and chain with more attractive hoops or studs. You will only stop keeping ornaments in your nipples if you get married and your husband asks you to let your piercings grow over. If you never marry or if you fall in love with a man who likes pierced tits, then you keep them forever.

Yours, Craig

This was what he had been doing while she had been bound to the chair for so long waiting for him to return and pierce her second nipple. As she had been sitting there, she had believed that she was only suffering a play piercing; she had no idea that he was making them permanent. And now they were permanent. He was right. She had earned the seventh envelope and she had to obey this instruction. She deserved to pay a full measure of punishment.

Leslie pulled her dress off over her head, being careful not to jostle the lock that hung from her nipples and looked down at the ugly safety pins that had been thrust through them so cruelly. They were full-sized steel pins and, with their mangled ends crimped flat to secure the points of the pins, looked even uglier than most safety pins. And the chain was nothing special to look at, either – just a foot of quarter inch chromed steel welded links.

She would have to be careful not to snag the pins or chain, especially when she was sleeping.

She unlocked the padlock from the chain, freeing her house key, then unlocked the belts from her crotch and waist. Removing the anal plug was more difficult than she expected, all the lube having been absorbed long ago, but, once she got it moving, she was able to work it out with a tolerable amount of pain. She saw only one small smear of blood on it. She felt herself carefully. Her asshole was gaping open, but she could feel it slowly beginning to contract again.

Next, she gently pulled the dildo out. It came smoothly and easily. Though it had been inside her all day, she was still excreting enough lubrication of her own to make it slippery.

It felt great to be empty below the waist again.

She wished that she could free her nipples, too, but that would never happen. The only thing that she could look forward to was getting rid of the chain in the fall and replacing the ugly pins with discrete studs.

She limped back into the kitchen, turned her calendar forward by three months and circled the third Saturday of the month. That was the day that she could remove the pins.

She had never liked the look of pierced nipples, but, unless she fell in love with a man who felt the same way and married him, she was going to spend a lifetime acquiring a taste for them.

An hour later, after showering, brushing her teeth, and cleaning her new piercings with alcohol – the first of many such cleanings that she would have to perform – and protecting the wounds with two Band-Aids, she climbed into bed.

She cried herself to sleep within minutes.

She had never felt happier.