A Lady Pays Her Penalties Read online

  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 going to hate performing it more than suffering 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. It will cause me considerable discomfort. If this is the last envelope, I will have to endure that discomfort until I walk home from here. If this is not my last envelope, 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 striped ass toward Craig, and spread her legs wide, exposing her puckered asshole for his viewing 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 anus. 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 base 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. Occasionally, she wiped the sides of the plug against the edges of her hole to transfer 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.

  She remained bent at the waist, patiently waiting for him to finish his inspection.

  When he finally stepped back, Leslie slowly stood erect, adjusting to the feel of the big plug that filled her anus. She walked cautiously into the bathroom, taking small, wide steps, and returned with another bath towel. She laid it on the bed, lay 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 molded, realistically detailed, black dildo was not. To avoid tearing, she would have to stimulate herself to get enough natural lubrication to let her work the full eight inches of heavy black silicone inside. She was already somewhat wet after 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, millimeter-by-millimeter, it was sliding a little deeper with every thrust; her cunt was 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 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 that was now 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 the crack of her ass.

  She turned back to face the bed and picked up the black leather harness. First she buckled the belt tight about her waist, and 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 and there was no way that she could remove the belt until she removed the padlocks. According to her instructions, the keys were inside her house so she had no way to free herself of her “double stuffing” until she returned home.

  She would be double-fucked constantly until the remainder of her punishment day was over.

  She put her legs together as best she could with 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 a 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 terrible 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 latex 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 cr
ying 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 the pin and me. 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, and 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.

  Her breaths were short and sharp, sounding almost like dog panting.

  She listened to his movements. She heard his quiet footsteps walking away, and then the rustle of a pair of latex gloves slipping onto one hand then the other. She held her breath to listen more closely and heard the cap of the alcohol bottle scrape a little as he removed it. 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 the chemical, 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 a tenth of a millimeter at a time.

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

  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 are 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, the blunt point tented her sensitive skin 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, the shaft is unpolished. 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 slowly emerged from her flesh.

  Finally, she felt him slide an end link of the small chain over the pin, and 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 slowly, careful to avoid moving her breast. If she made the chain swing, her agony would be amplified.

  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 in the same way. And, after that, she still had to serve two more penalties today. The worst was yet to come.

  She could not have forced herself to eat even if she had 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 did not know if she wanted him to come back sooner or later.

  She strained to hear if he was coming 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.

  No. Today was Saturday, tomorrow Sunday. It would be two days before businesses were open again.

  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 it was not Craig coming into the room? She had not heard her car return outside. 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 was Craig, but remained silent. She would know soon enough – and if it were not, she could do nothing 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 for 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.