A Lady Pays Her Penalties

by Ashley Zacharias

She sobbed and begged. If he had a heart, her pleas would have broken it. But Leroy did not have a heart.

  When he finished, she made one last plea. “If you’re going to do this to me, please gag me again.”

  That wish he granted.

  When he pushed the peeled pepper into her cunt, she shrieked like a banshee through the gag and every muscle in her body convulsed as though she were suffering a grand mal seizure. The pain must have been incredibly intense.

  To maximize her agony, he worked the pepper in and out of her cunt and rolled it around to ensure that it made contact with every side of her female orifice.

  When every part of her insides had come into contact with the burning fruit, he pulled it out and rubbed it through the folds in her inner and outer lips and then he took care to rub it back and forth over her clit for a long time, pulling the delicate hood back to make certain that the most sensitive part of her female anatomy was well-coated with the terrible juice.

  If The Whore had not been gagged, the neighbors would have summoned the police for sure. She sounded like she was being tortured to death. She felt like she was being tortured to death.

  He set the used pepper on the table next to the bent pimp stick, and then he drew the cucumber from her ass and set it beside the pepper. “You’re lucky that I don’t make a cucumber and pepper salad and make you eat it,” he said.

  But she didn’t hear him. She was lost in a sea of agony. The pepper was gone from her cunt, but its oily juice remained. Her cunt would keep on burning for a long, long time.

  He unwrapped the wire from her ankles and she pressed her legs together and brought her knees to her chest. Then he unwrapped her wrists and she grabbed at her cunt with both hands and curled into a ball.

  When he pulled the tape from her mouth, she said nothing; she continued to sob and sob without pause.

  He left her on the table and went upstairs to look at her wardrobe.

  When he returned to the kitchen a quarter hour later, she had not moved.

  “Get up. We’re going for a little ride,” he said gently.

  She kept clutching her crotch as she struggled off the table. The burning in her cunt had barely diminished; the torture was not going to end.

  He was afraid that she wouldn’t be able to walk, her legs were twitching and convulsing so badly, but she managed to stay on her feet.

  He escorted her to the garage. He had turned his car around and backed in. The trunk was open. He helped her climb inside. She curled into a ball. He closed the trunk lid gently, being careful that her toes and fingers did not get mashed.

  * * *

  It was hot and stuffy in the trunk. She could not keep from bouncing around, sliding forward and backward when he braked and cornered. Those were the least of her concerns. Her womanhood was burning like the fires of hell and she was naked. If he dumped her by the highway on a Sunday morning like this, she would be arrested for sure. And probably be raped first. But the man who stuck his dick into her capsicum-soaked pussy was going to be in for a hell of a surprise. As would the medical expert who performed the chemical analysis on her rape kit.

  When Leroy – it wasn’t time for him to be Alex yet – finally stopped the car, he opened the trunk and told her to get out.

  Though she was as naked as the day she was born, she obeyed.

  They were on a country road. There were no other cars in sight.

  “Home is that way.” He pointed to the east. “You can wear this.” He threw a scrap of cloth at her.

  She shook out the cloth and saw that it was one of her summer dresses, a flower print shift that buttoned down the front. But when she covered herself with it, she saw that all the buttons had been removed – she would have to hold it closed all the way home – and the bottom had been chopped off, leaving a new ragged hem that fell at mid-thigh rather than at its original mid-calf length. Just as bad, much of the back had been chopped away, displaying her newly flogged body to all the world; and the neckline had been chopped low so that she had to reveal more cleavage than was modest.

  Before driving off, Leroy said, “By the way, I expect you to earn that missing hundred dollars before you get home. If I see you back at my crib and you’re still short, I’m gonna sell you to Leon. I hear he really knows how to make his slots pay off, night after night.”

  As he sped off in his car, she began trudging down the shoulder of the road, clutching her butchered dress closed with both hands. Her feet were tender and the gravel was cutting them. She moved to the edge of the pavement but that was only marginally better; the asphalt was sharp in places.

  She had to hold the dress closed at her bust with one hand and closed at her hips with the other. As she limped along, stray gusts caught the ragged hem of the lightweight fabric and blew it high around her legs. She didn’t think that she was actually flashing the occasional passing car, but she held it closed directly over her crotch to minimize the risk of public obscenity. The front gaped open at her midriff but there was nothing that she could do about that.

  She was keenly aware that her back and thighs were striped with welts from her beating and that the chopped up dress revealed her punishment to anyone who looked closely enough.

  Her cunt continued to burn like hell. She wondered when it would stop. How long would it take for her natural juices to wash the burning oil away? Hours? Days? She wondered if her nerves would grow numb from the assault before the oil was gone. Maybe she would feel all right tomorrow, but Alex would get a horrible shock if he tried to make love to her. The thought was almost enough to make her smile.

  She still had to earn her final hundred dollars and she wasn’t going to be able to do it with her cunt. She’d have to take her john in her ass or suck him off. Her ass was aching from the assault with the cucumber, but it was stretched loose enough to take a man with ease.

  She thought about having to earn another hundred dollars before she got home. As she originally conceived the rules, she would only have to earn money on her whore day, not during her punishment day. But the nature of her punishment was left to Leroy’s discretion. She had given him guidelines in her letter, but had made it clear that those were only suggestions; he was free to innovate however he liked, including ignoring her guidelines completely. If he wanted to force her to service another trick, or more than one, that would be a legitimate part of her punishment.

  The more she thought about it, the more she liked the idea. She didn’t like having to do it but that was all right. She was not supposed to like her punishment. But she did like the concept. It was an appropriate consequence for losing the game.

  * * *

  She had been limping along the side of the road for more than an hour when she reached the outskirts of town. Her feet were bleeding and she was exhausted from her extended ordeal. She heard a car pull up beside her and looked to see Alex in his gold-colored Accord.

  He rolled down the passenger window and she leaned in to talk to him. “Hello.”

  “Hi, there. You look like you need help. Can I offer you a ride somewhere?”

  “I’d sure appreciate it.” She wondered if her punishment were finally over. Was it already noon?

  “Well, then, hop on in. I’m John.”

  She did. And, as she climbed into the car, she thought, “John” not “Alex”. It must not be noon yet. A glance at the dashboard clock confirmed that it was still only ten-thirty.

  There was ample time for an eternity of pain yet this morning.

  Her beaten back, ass, and legs stung fiercely when they came into contact with the car seat, but she wasn’t complaining. It was better than walking down the road in bare feet.

  She released the front of the ruined dress and it fell open across her legs to reveal her belly and pussy. Though her cleavage now extended down to her ankles, the bodice stayed draped loosely over her breasts. If she didn’t move too much, her tits would remain covered and she wouldn’t shock passing motorists.

  John looked across at he
r partial nudity and said, “Wow. You’re sure a good-looking woman. What do you do for a living?”

  She laughed through her pain and humiliation. “Just what it looks like. I’m sure grateful for this ride. I’d like to show you my appreciation in a more substantial way.”

  “Gosh, that’d be terrific.”

  “It’s just that I can’t give it away. There’s union rules. My daddy’d beat me to a pulp if I didn’t ask you for compensation.”

  “I’d hate to see you get hurt. I might be able to give you a few dollars. How much do you want?”

  “Well, that depends. What would you want to do?”

  “I don’t know. Whatever you do best.”

  “I’m a terrific cocksucker. I can give you the best blowjob that you’ll ever have in your life. Believe me, I’ll put everything I’ve got into it. I can do that right here in your car. We won’t have to get a room or anything. But, if that’s not what you want, I can let you fuck me in the ass. Some men find that special and I’m real good at that, too.”

  “Gosh, I’d be happy to get serviced right here in my car. The blowjob sounds fine.”

  “You won’t regret it, I promise. You have a hundred bucks?”

  “That seems kind of expensive.”

  “You won’t think so after you’ve felt my lips working down your cock. If I don’t give you the best blowjob you have ever had, then I’ll give you your money back. Not many whores offer a money-back guarantee.”

  “I can’t complain about that.”

  “Then why don’t you find a quiet place to park and let me get to work?” She licked her lips. “I can’t wait to taste you.”

  “I know somewhere special.”

  “Where’s that?”

  “You’ll see when we get there. It’ll be especially exciting for you.”

  The Whore’s heart sank. She was in agony already. Leroy’s idea of an especially exciting place for her to give a blowjob had to involve more punishment. She forced a smile and said, as brightly as she could, “Okay. Let’s go.”

  He drove around a block and pointed the car back down the highway in the direction from which she had been walking. After a few minutes, they passed the place where Leroy had dumped her from the car an hour ago. Her heart sank even lower. If John kicked her out of the car after getting his blowjob, she’d be walking even further than when she started.

  John kept driving away from the city for another ten minutes.

  He commented darkly, “This had better be a terrific blowjob.”

  “It will. The best ever,” she promised, forcing herself to sound as positive as she could.

  The car began to climb. John continued driving until they were far up into the hills that surrounded the city. He found an overlook and parked.

  “Come on,” he said as he got out of the car.

  “I thought that you wanted it in your car,” she replied as she got out.

  “Nah. Changed my mind. Too crowded in there. I’d like to be breathing nice clean air when I get sucked off. Wouldn’t you?”

  “Sure.” She followed him across the road and into the bush on the other side. Sharp sticks, rocks, and thorns punished her feet even worse than the gravel beside the road. They climbed twenty feet to a small outcropping of rock. From here, she could see the city spread out beneath the hills.

  A light scrim of trees and underbrush sheltered them from the road below. If anyone stopped at the viewpoint, they would not see her and John. Not unless they decided to cross the road and climb a little. If they did that, they would find a private little sex show almost immediately.

  John lowered his pants and underwear to his ankles and sat on the rock. His dick was limp. She remembered working on him only three hours earlier and feared that he might not yet be sufficiently rested to get it up again. She was terrified that failure out here would earn her some punishment that was more awful than what she had endured already.

  “Why don’t you shuck that bitty little dress and show me what I’m buying for all that money?” he asked.

  The Whore held out her hand and said, “You haven’t bought me yet. Nothing happens until I have a hundred dollars in my hand. After that, it’ll be wonderful.”

  “Shucks, darling. I wouldn’t cheat a whore. You’ll get your money.”

  The Whore was vividly aware that she was alone with this man, far from any help. And that she had no way of predicting what he would do. And that he was far stronger than her. Being raped and beaten could be the next part of her punishment. She hoped that John/Leroy would show a touch of human mercy for once today. “I just want to get the messy business part of our party out of the way first so that we can concentrate on the fun part without having to think about it again.”

  He looked at her for a long minute, then shrugged and said, “Okay. I guess I understand that. Here, you go, darling.” He took a hundred-dollar bill from his wallet and handed it to her.

  It was undoubtedly one of the very same bills that she had earned yesterday and had been forced to return to Leroy a few hours ago. It seemed unfair to have to earn the same money all over again. But this was her game and her rules.

  Them’s the breaks.

  She didn’t have any pockets so she shrugged her useless dress off her shoulders and folded it up, wrapping the precious bill in the middle of the resultant package.

  Then she dropped to her knees in the dirt in front of her john, took his limp cock in her hand and began gently licking the head, swirling her tongue around and around. Miraculously, it began to rise to her charms. She began to weep with silent relief as it got stiffer between her lips. Why couldn’t she have managed this a few hours ago and saved herself so much grief? She lowered her head and began taking him into her mouth as deeply as she could, working on swallowing her gag reflex and getting her lips right down to his root.

  She worked on his cock for a long time, trying to ignore the occasional automobile that passed on the road below. They sounded so close. There might be gaps in the brush that allowed glimpses of the naked whore performing fellatio on her john, but she couldn’t look around and see. She didn’t want to know; she didn’t need any more humiliation. She put all her concentration into her work, outdoing herself to fulfill her promise to give the man the finest blowjob of his life.

  Her recent practice helped. She had come to realize that what she did with her hands around the base of the man’s penis was at least as important as what she did with her lips and tongue.

  His moans grew in volume and tempo, attesting to her newly acquired skill, until he finally gave a mighty groan and came in her mouth. Comparing this with her other recent experiences with oral sex, she could tell that the amount of his spunk was small and his ejaculation weak. That was no surprise. This was the sixth time this cock had been called to duty in less than twenty-eight hours. It must be drained about as dry as a man’s cock can be.

  She swallowed what little he had to offer, licked him clean, and stood up. “Thank you,” she said, wondering if he was going to demand his money back. She would fight to defend her hard-earned fee. He would have to beat her unconscious to get it back.

  Leroy might just do that.

  When John said, “No, ma’am. Thank you. I can’t say for sure that it was the best blowjob of my life – I’ve had some damned fine blowjobs lately – but it definitely ranked in the top three. You’ve earned your money, all right.”

  Her relief was palpable. “It has been my pleasure to serve you, sir. A true pleasure.”

  Her cheeks were wet with fresh tears – more from relief than from the pain of her still-burning cunt and the stinging welts on her legs and back.

  He pulled his boxers and pants back over his hips and began walking down the hill through the brush.

  She pulled her dress back over her shoulders, being careful not to lose her precious money, and followed him. Her feet were further punished by the quickness of his pace, but she didn’t dare lose him now.

  When they got to the
car, she opened the passenger door.

  He was standing on her side of the car and slammed her door shut as soon as she opened it. “Where do you think you’re going, ma’am?”

  “I thought that you’d give me a ride back to the city. You were going that way when you picked me up.”

  “I am going that way, ma’am. But I don’t need no passenger. You don’t see a taxi sign on my car, do you?”

  “Please, mister. You brought me all the way out here. I did my best for you. You can’t leave me.” It would take all day and most of the night to walk all the way back to town from here. Her feet would be shredded like bloody hamburger before she made it halfway home. She’d be walking on naked bone by the time she made it to the city limits. If she made it that far. She’d more likely be gang raped and murdered out here in the wilderness.

  Streams of tears were flowing down her face.

  There had to be some spark of human mercy somewhere in her husband’s heart.

  The John’s eyes gleamed. “I’ll tell you what, ma’am. I could give you a taxi ride just this once.”

  “Thank you,” she said with relief.

  “But, of course, you’d have to pay the fare.”

  “The fare?”

  “Yes, ma’am. Like you said, there’s union rules. I can’t give you a ride for free. If I’m going to offer a taxi service, I got to collect a fare.”

  “What kind of fare?”

  “Well, ma’am, I’m not a regular taxi. No meter or anything. I’m more like a private limousine service. That’s expensive. And it’s a long drive back to town, as you know. I can drop you right at your front door, but it’ll cost you a hundred dollars. I know that seems like a lot but I’m pretty sure that you can afford that much; a nice professional lady like yourself has to have a hundred bucks on you.”

  She looked at the bill clutched in her hand and began to cry harder. “I can’t give you this. I owe it to someone else.”

  “No, ma’am. If you want a ride back to town, you owe it to me. But, don’t fret. I don’t mind if you keep your money and find another way to get back. It don’t matter to me. But decide quick, because I gotta go now.” He walked around to the driver’s door and slid into the seat.