A Lady Pays Her Penalties Page 9

  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 groaned at the sight of her mutilated nipples.

  Then she held up five fingers.

  * * *

  Craig tore the fifth envelope open.

  The instructions 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 troubled by the new situation that Leslie had put him in. This was the first time that she had done anything in public; and 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 killed. 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 anything he said 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. You’ve helped me 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 go 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, whatever you tell them. It’ll be cool.”

  Craig gathered her clothes, 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.

  A fool can always find ancient wisdom to justify his foolishness.

  But he was staying with her 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 let it settle around her body. The neck scooped low enough to show ample cleavage, almost revealing the tops of her areoles. The safety pins and chain connecting them made some odd bumps but they were small; 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 largely unnoticeable unless you knew to look for them. In the same way, the locks on the waist and crotch straps made slight bumps around her hips, 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 few minutes, 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 mentioned 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. By the time she made it back to her house, they would feel like instruments of torture worthy of the Spanish Inquisition.

  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 eyeliner and mascara made them look as big as saucers.

  A multitude of bobby pins kept her wildly teased hair piled high on her head.

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

  Finally, she pulled a regular-sized padlock from her suitcase and set it on the table with a heavy thump. 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. Every step was a unique exercise in discomfort because of the objects stuffed into her cunt and asshole, the strap pulled tight between her legs, the pain from her damaged ass and tits, and the high heels fixed to her feet. 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, on top of whatever time she spent completing the last penalty. By the time she finished, she would be in utter agony. These indeed were six envelopes filled with punishment.

  And that presumed that she did not encounter any additional delays. 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, much less an expensive luxury car.

  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 house 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 someone, then you can separate the two halves of my keychain and use the last padlock to lock my house key to the chain betwee
n my nipples. Use my car key to drive yourself to my house to pick up your car. I will walk home.

  * * *

  Craig guessed that car salesmen would not be eager to let a slutty-looking single woman test drive a car and he had been right. But he had not anticipated Leslie’s resourcefulness. She knew that she faced rampant sexism, but figured that she could make that work in her favor if she were willing to debase herself.

  First, though, she had to get 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 rubbed against her nipples and irritated them more with each step as it slid back and forth; and it rubbed across her stripped ass with equal roughness. 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 not feel even the briefest moment 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. This was not accidental – she had reasoned that she was less likely to catch a sexually transmitted disease from oral sex than from the regular kind – but the necessity of using her mouth posed its own problem. She was not a complete novice, but she was far from an expert fellatrix. In truth, she had engaged in oral foreplay with men on a few occasions, but had only once sucked a man off to completion. And, that one time, she had not been an entirely active participant. This time, she was going to have to do the work and she was not entirely certain how to do it. She could only pray that she would receive divine inspiration when the chips were down. Or, to be more accurate, when she had gone down.

  Life is filled with opportunities to learn new skills.

  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 let her penalty to be only to talk a salesman into giving her a test drive without having to include a blowjob.

  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 late Saturday afternoon, the place was busy. A small squad of salespeople was attending to a flock of other customers – mostly families with small children. She dared not bend over to look into windows and study the vehicle interiors for fear that she would flash her crotch harness. Her new worst fear was that, if she bent over even a little, some kindergarten-aged girl would start pointing at the black leather between her legs and shouting, “What’s that, Mommy? What’s that lady wearing?” She stayed as erect as possible while she 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 the practicality of performing fellatio were the primary goal of every wife who walked onto a car lot with her husband, there would be far fewer sports cars sold to men in the throes of their middle-age crises; 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”. Leslie thought that she could detect a grimace of disdain in the corners of the woman’s mouth and imagined the pin on the plaque piercing more than the fabric of her blazer. The image helped her return the woman’s insincere smile.

  Behind her smiling mask, Leslie was cursing her bad 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.” The woman shrugged the plaque on her tit toward Leslie.

  “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 sales bonus. No sale, but a wonderful bonus.

  But, before any of the salesmen on the floor 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 baldpate with a combover of straggly gray hair that was held in place with an excess of mousse. He wore no wedding ring, but looked as married as any husband alive.

  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 patronize prostitutes, but not so faithful that he would turn down a free blowjob.

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

  The two men looked at each other, and then slowly appraised her from pink high heels on her feet to hair piled high on her head. 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 explain 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 exorcise his initial impression. Now he was willing to bel
ieve 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, bringing 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.