A Lady Pays Her Penalties

by Ashley Zacharias

  As soon as he let her into the room, she said, “You can leave a hundred dollars on the table for me.”

  He obliged without comment.

  She led him to the window and turned him so that he was looking out over the city. Standing behind him, she asked, softly, “What would you like me to do for you? For what you paid, you can have any service that you wish. I want to do something special for you. Something that you did once before and liked so much that you’ve always wanted to do it again. Or something that you hinted to your wife that you would like to try and she ignored your need. Or something that you read about but never dared mention out loud. You can use any part of me. Ask me to assume any position. As long as you don’t injure me, anything is yours for the asking. You have never had a woman before who is as available to you as I am right now. Whatever your fantasy, it can be reality tonight. I know how much variation men want and I won’t be surprised by anything you say. I promise.”

  Her speech made him hard. He hadn’t known if he had it in him to get it up again today, but The Whore was a miracle worker. And the biggest miracle of all was that he didn’t know why. He wasn’t imagining any particular act. There wasn’t a single fantasy that dominated over all others. The whole day had been more than he had ever fantasized about. But the idea that this woman, this perfect whore, was prepared to do anything, follow any instruction, made him hard. When she held him from behind and caressed his manhood through his pants, he believed every word she said. He believed with all his heart that she had fucked a thousand men in a thousand ways and had experienced every imaginable perversion. He believed that anything that he might suggest would seem tame compared to the outrageous things that she had done with other men.

  Finally, he spoke. “I don’t know. You’re the expert. What do you suggest?”

  She whispered in his ear, “I’m going to lay you on that bed and blindfold you so that you can concentrate on nothing but what you are feeling. I’m going to suck you until you are as hard as a rock. Then I’m going to straddle you and slide my cunt down over your cock. When I start to fuck you in earnest, I’m going to slide two fingers as far into your asshole as possible and I’m going to massage your internal male gland until you come like you’ve never come before. You have never had an experience like that, have you?”

  He shook his head.

  “It will feel exquisite. Do you want to find out for yourself how exquisite a prostate massage feels when you’re cumming?”

  He nodded his head.

  “Take your clothes off and lie down on that bed on your back.”

  While he was undressing, she pulled the covers off the bed and slipped her dress over her head. Her only underwear was a pair of black pantyhose with no crotch in them. The crotch was not cut out; the pantyhose had been manufactured that way. Where could a woman buy underwear like that?

  She pushed him back on the bed and pulled a black cloth from her black clutch. Gently, she tied it around his eyes. It was not a particularly effective blindfold, he could see light coming in around his nose and make out shapes if he squinted, but he decided to close his eyes and go along with the experience that she had described.

  “Feel my tits caress your cock. Doesn’t that feel nice and soft?” he felt her soft, warm, smooth, pillowy breasts rub gently against his cock. He was not completely erect – he had lost a little wood during her preparations – and the gentle caresses were not stimulating enough to bring him back completely. He wanted to feel her lips and tongue on his manhood.

  Because he kept his eyes closed under his blindfold, he did not see The Whore’s practical reason for massaging his cock with her breasts. While she was doing leaning over, rubbing against him, she was unpacking two more items from her purse: a latex condom and a small tube of lubricant. She tore the little foil envelope open and removed the condom. Then she unrolled it over the index and middle fingers of her right hand and squeezed a generous dollop of lubricant on the end. She reached between her legs and smeared the lube over her cunt. She squeezed a second dollop of lube on her condom-covered fingers as she moved her head down to start licking his cock. Putting the lube aside and holding her right hand with the condom-covered fingers out of the way, she used her left hand to squeeze and pump the man’s shaft until he was fully erect. His hard on seemed a little iffy to her, so she straddled him and impaled her cunt on it as soon as she could. She began grinding up and down slowly while squeezing his cock with her cunt as hard as she could. She knew the value of Kegel exercises for strengthening the peritoneal muscles and had been practicing them sporadically for years. She was not as strong as she should be, but she was stronger than most women and could give her man that little bit extra stimulation that he needed in a pinch.

  Once she had established a rhythm, she stretched back and slid her lubricated, condom-covered fingers down his ass crack, feeling for his anus. It took a bit of feeling around before she found it, but once she was sure of its location, she rubbed the lube into it and then began pushing slowly and inexorably into him. He groaned loudly. She took that as a sign that she was doing the right thing. She felt rings of muscle tighten against her fingers but she did not relent. She kept working her fingers around, bending and straightening them slightly, massaging the muscles that were working to constrict her. The man beneath her kept groaning more and more loudly. She told herself that she was hearing passion in his groans and kept working her fingers deeper. She felt when the sphincter muscles finally relented and her fingers slid all the way to the last knuckles without further resistance. From her study of the diagrams in the sex manuals, she knew that the prostate gland was on the wall closest to his testicles so she bent her fingers up and felt for the bulge.

  The prostate gland is where the fluid part of semen is produced. The nerves to the penis run around it. She had read that the sensation for a man of having his prostate massaged during sex was exquisite. She hoped that was true. She didn’t want to press too hard for fear of damaging something, so she kept giving him a constant gentle massage. Even if it wasn’t doing too much good directly, she was stretching his sphincter muscles and that had it’s own erotic component. And there was always the good old placebo effect. If the man believed that he was receiving special erotic treatment, then he was.

  Her fingers were growing tired when he finally came. He screamed in ecstasy. She had never heard him scream before; obviously she had done something right.

  She did not bother simulating an orgasm herself. This was an act performed purely for his pleasure. Instead she gently withdrew her fingers from him and pulled the condom off, turning it inside out. Before dismounting, she said, “I love making a man come hard like that. Did you like it as much as I did?”

  He mumbled something incoherent, but she understood that he was affirming that he had liked what he had experienced.

  Less than a minute later, as she was walking out the door, she said, “I’m glad you came. I’ll see you around.”

  He was still lying on the bed, naked, moaning with pleasure as she shut the door on him.

  Four hundred dollars earned so far. This was probably enough to satisfy the quota but it would take two hundred more to make her absolutely safe. She wanted that safety because the punishment that awaited failure would be too severe to leave to even a one-in-six chance.

  This time John’s erection had definitely been questionable and the orgasm had taken a long time and a considerable effort from both of them. The next one would be a definite challenge.

  This game was going to get a lot more interesting before it was over.

  * * *

  The Whore felt a chill when she got out of her car. It was almost eleven and the temperature had fallen considerably. Her fishnet stockings provided little insulation for her calves and lower thighs; the gap of naked flesh that was exposed between the tops of the stay-ups and the hem of the micro-miniskirt had no protection at all; nor did her bare midriff or naked shoulders below and above the hot pink, too-tight tube top.
The wind that blew up her tiny skirt felt like it was raising gooseflesh on her naked pussy. The only part of her that felt warm was her head because it was well protected by the blond big-hair wig. Her eyelids felt heavy; the upper lids were spackled with bright purple eye shadow and burdened with thick false eyelashes that were loaded with a bountiful application of mascara. Her lips were sticky with multiple layers of vermilion lipstick.

  Walking down the street, looking at her reflection in the dark vitrines, she barely recognized the streetwalker’s hardened face staring back at her.

  She had thought long and hard about how to stage this scenario. The streetwalker was at greater risk than other whores. There were many things that could go wrong if she was out alone on the street for even half an hour. Mostly, she had to worry about the three P’s: pimps, police, and perverts.

  At first she had planned to send John to a deserted part of town, a well-lighted street corner in a residential neighborhood. The problem with that was police and perverts. The residents were likely to call the police if they saw an obvious hooker loitering outside their house. Worse, in a place with no other people on the street, she was likely to be hassled, maybe even violently assaulted by passing perverts who would see her as an immoral woman who was vulnerable and deserved punishment.

  After looking for a more suitable venue, she finally decided that it would be safest to bite the bullet and head straight to Broadway where all the rest of the streetwalkers hung out. She would explain her circumstances and come to an understanding with them.

  Instead of avoiding the other girls that were standing around, waiting for customers, she walked directly to the two nearest, youngest, hardest-looking hookers and introduced herself.

  “Hi.”

  “What you doing here, ho? You one of Leon’s new girls?” The woman who asked was a short, busty Latina wearing boots, a miniskirt, a fur bomber jacket, and a lot less makeup than The Whore. The fur jacket was sensible; she didn’t look like she was freezing half to death.

  “No. I’m here on a private gig. Don’t worry. I’m not going to take any business away from you. The only man that I’m going to go with is my husband. He should be along in a few minutes. I’ll get right in his car and then you won’t see me again. And if he doesn’t show, then I’ll be on my way alone. I won’t be talking to any men that you’d be interested in.”

  “Yeah? Maybe we’d be interested in your husband. Maybe, he’d be interested in us.” This time it was the other woman, a brunette with bad acne scars, who spoke. She couldn’t be more than twenty years old.

  “He won’t be interested in you when I’m standing right here.”

  “Then maybe you should get lost before he comes around and we’ll find out what does interest him.”

  “He wouldn’t chance it, knowing that I’m supposed to be somewhere around here.” The Whore smiled. “But maybe if he sees you with me, he’ll decide to come back some other night and do business with you when I’m busy at work. I think he’s faithful, but you might find out otherwise.”

  “Maybe,” the Latina said. “But maybe Cherry and me’d be better off finding out for ourselves tonight.”

  “The bottom line is that we got business to conduct and you’re in our way. You aren’t welcome here so you can get lost now, not later,” the brunette said.

  “I’ll give you each twenty bucks to let me stand here and not hassle me until my husband comes around. That’s pure profit. You don’t have to do a thing for it and, like I said, I’m not going to cost you a cent in other business.”

  “Forty bucks each,” the brunette replied.

  “That’s eighty bucks. I bet a man could buy your services for that much.”

  “That’s what you’re doing, ho. Except that a man would pay us to screw him. You’re paying us to not screw you,” the Latina said with a grin.

  The Whore sighed. “Okay. Forty each, but you got to make sure that the other girls around here don’t hassle me, either. I can’t afford to pay every girl on the street what I’m paying you.”

  “Don’t worry about that, ho. This be our corner. What happens on our corner is our business.”

  “Your corner and Leon’s,” the Whore replied as she handed two twenties to each of the other women.

  “Yeah, well, Leon’s another thing. He’s not going to be happy if he sees you here. You gonna pay a heavy tax if Leon finds you on our corner. I don’t think he’s going to buy your slumming housewife shit.”

  “Shit, we got a hot one. It your turn, Angel.”

  The Latina walked to the car that stopped by the curb and waited until the window rolled down. There was a brief conversation, and then she returned.

  “No deal?” the brunette asked.

  “Guy had vice cop written all over him,” the other replied. “I think I recognized him from the twenty-fourth.”

  “He would have arrested you?” The Whore asked, wide-eyed.

  “Not likely,” the Latina replied. “He was so horny was has almost creaming his pants. I would a been sucking him off for free for half the night. Leon gets unhappy when that happens. And when he’s unhappy, he makes me unhappy.”

  “Does he beat you?” The Whore asked.

  The other two girls laughed. “No, ho. He don’t need us to get marked up. That’s bad for business. He bogarts our candy is what he does. I can’t be happy when I don’t get my candy. It’s my candy makes me mellow,” the Latina replied.

  “Oh.” The Whore didn’t think that the Latina seemed particularly mellow. But before she could reply, she saw John’s gold Accord rolling slowly down the street. Showtime. “This one’s my husband,” she told the other women. “I’ll be out of your hair in a few minutes.”

  “Can’t be too soon for us,” the brunette said seriously, but The Whore didn’t hear her; she was already halfway to the curb.

  “Looking for a party?” she asked when John rolled down his passenger window.

  “I don’t know,” John replied. “What do you charge?”

  “A hundred bucks.”

  “What do I get for that much?”

  “I can’t–” The Whore started to say but she was interrupted.

  “This ho’s the best cocksucker on the street, mister,” the brunette said. “She can suck the chrome off a trailer hitch. No shit.”

  The Whore looked around in shock. Her two new friends had followed her to the car and were now standing on either side of her.

  “That’s not worth a hundred bucks, though,” the Latina said. “A blowjob’s only worth thirty. Forty if I do it because I’m special good. I’ll tell you what a hundred bucks will buy you. It’ll buy this ho’s asshole for you. That’s what you really want. You want to fuck this ho up the ass.”

  “Yeah,” the other woman said before The Whore could speak. “That’s this ho’s special thing. She’s a regular Einstein with her asshole. An artiste of the ass, so to speak. No cock’s too big for her to handle. You can pound her deep and hard and she’s so hot and tight, you’ll think your dick done died and gone to heaven. Ain’t that right, ho?” The woman grabbed The Whore’s ass and squeezed hard enough to hurt.

  Despite the eighty dollars that she had given the two women, they were going to screw her over in the end anyway.

  “That’s right,” the Whore answered, appalled to see a feral gleam in the John’s eye.

  “What’s right?” the Latina asked.

  There was a long pause, and then The Whore had to say, “You can fuck me in the ass for a hundred dollars.”

  “How can he fuck you?” the brunette asked.

  “Hard and deep,” the Whore replied, trying to sound enthusiastic.

  “I think I’d like that,” John replied, sincerely.

  Leslie was not an anal virgin. Once before in her life, she had been penetrated anally. She had not liked the experience and did not care to repeat it. But she had made the offer and was trapped now. She couldn’t disappoint The John. Or Leroy. Failing to make her quota would brin
g down on her a lot worse shit than a vigorous ass fucking.

  “I tell you what you do with this ho,” the Latina said. “You take her to Jack’s down around the corner and you rent a room for a couple of hours. Don’t let him charge you more than fifty bucks for two hours. And you take this ho up to that room and you bend her over the chair. Jack’s a shitty flophouse but he’s got nice solid beds and chairs because they got to take a lot of abuse. You bend her over the back of that chair and you flip her little skirt up out of the way and then you drive into her pretty little asshole like a pile driver and you pound her ’til your cock feels like it’s done gone to heaven.”

  “You think you’d like doing that?” the brunette asked him.

  “Yes. I think I would,” The John said happily.

  “Sure you would,” the Latina said. “You’re going to love it. Really love it.” She took a foil-wrapped condom out of her purse and tossed it on the seat beside the john. “Use this. It’s already lubricated. That’ll be all that you need to get into her tight little asshole. I know. I been there myself. More than once.”

  “Yeah,” the brunette said. “And if she yells a little bit, that just shows how much she’s loving it. This ho, here, she lives for servicing men like you. She gets off on ass fucking, don’t you, ho?”

  “Yes,” the Whore said, trying not to sound as dismayed as she felt. “I’m going to love it so much that I’m going to scream about it.”

  “Okay,” The John said. “I’ve got my hundred dollars ready. Hop in.”

  The Latina opened the door for The Whore and the brunette helped her into the car.

  As they drove away, the Latina said, “Maybe that’ll teach the snotty bitch to come down here and mock us.”

  “Yeah,” the brunette laughed. “And she thought that her husband was going to be thrilled just to get a quickie blowjob. She’ll learn different now. He’s going to get a real thrill tonight.”