Punish Me, Please Me

by Ashley Zacharias

“You look like vice presidential material to me,” he said as he walked away, leaving her lying across her desk, crying loudly and gingerly rubbing her hands over her aching butt.

  * * *

  “How’s your ass? Still aching?”

  “That’s none of your business.”

  “It’s been a week so I’m assuming that it’s not too sore now.”

  “None of your business.”

  “I noticed that you didn’t spend much time in your chair last Friday but you spent most of Monday at your desk.”

  “None of your business.”

  “Being that I was the one who bruised it good, the state of your aching ass kind of is my business.”

  “Fuck off.”

  “Tch, tch. Such language from a lady.” Eli smiled out her window. “How’re your nipples?”

  “What?”

  “I’m assuming that they feel all right.”

  “That’s none of your business either.”

  “Actually it is. Time is short. The next SMC meeting is scheduled for Tuesday the ninth. Re-organization is on the agenda. That includes approval of the succession plan. You’ll be sitting in a bigger, softer chair by the following Monday. We’ve only got two more weeks to play our games and I want to make you a winner. I’ve got two good ones planned.” He stopped talking and smirked at her credenza.

  “Well?”

  “Well, what?”

  “What kind of games?”

  “Card games, both. Games of chance. This Thursday, it’s going to be a pain game, next Thursday a sex game. Luck is important for a manager so we’re going to see how lucky you are. There’s a chance that you won’t feel any pain at all and a chance that you’ll suffer a lot.” He squinted like Dirty Harry. “So what about it, cunt? Do you feel lucky?”

  She sighed. “What kind of pain?”

  “No more pain than you suffered last week. But rather different in quality. It all depends on how lucky you are. At worst, you’ll feel like you’re suffering the agonies of hell but you’ll be able to stand it. At best, you won’t be hurt at all. That’s all I’m going to say. Be in your office at nine o’clock on Thursday night and I’ll give you a surprise.”

  An unpleasant surprise, she expected, but there was a vice presidency at stake so she’d do whatever he had planned.

  But she reserved the right to tell him to go fuck himself if he tried to demand too much. He had to be smart enough to realize that.

  * * *

  Eli laid a roll of duct tape, two wooden, spring-loaded clothespins, and a deck of cards on her desk. Then he pulled Keri’s desk chair into the middle of the room. Finally, he typed a web address into her browser.

  Her computer beeped.

  “Strip to your waist,” he said.

  “What are you going to do to me?”

  “I’m going to hurt you. Specifically, I’m going to hurt your nipples by squeezing them in these clothespins. You think that you can stand that?”

  She looked at the clothespins. “I guess so.”

  “If you want, you can find lots of videos of women getting their nipples clamped in clothespins on the web. It’s a pretty standard way of hurting a woman without causing serious damage. The pain is significant but not extreme. You won’t like it, but you’ll be able to tolerate it about as well as you tolerated the paddling last week.”

  She didn’t want to see any videos of women suffering on the web. He seemed to have done his research so she’d take his word about the consequences of having a woman’s nipples crushed by clothespins.

  She unbuttoned her blouse and stripped it off. Then she removed her bra – a skin-colored sports bra that was more comfortable than erotic – to free her ample breasts.

  Eli paused to stare at her in appreciation. She looked down and saw that her breasts were heaving because she was breathing heavily in her fear. Her pink nipples were already erect.

  Maybe that was why men like Eli liked to treat women sadistically: because a woman who was afraid resembled one who was sexually aroused.

  “Sit,” he said after taking a minute to enjoy the view.

  Her computer beeped.

  She sat in the chair.

  Middle managers were given desk chairs with arms; staff got no arms. He picked up the duct tape, tore off a long strip, and moved to tape her forearms to the arms of her chair.

  “What do you think you’re doing,” she demanded, pulling her arms away from his touch.

  “Put your arms back. I’m going to secure them so that you can’t reach your breasts and interfere with the game.”

  Her computer beeped.

  “No, you’re not.”

  “Yes, I am. Either you play the game or you don’t. But remember. If you leave without playing by my rules, then I still have time to screw you over with the Senior Management Committee. All I have to do is make an unsupported accusation of impropriety and they’ll withdraw their offer just to be on the safe side. It doesn’t have to be true. They’ll use it to turf you out when they stop receiving their User Analysis Reports. They love those reports.”

  She rested her arms back on the chair and let Eli bind her to it.

  When she was no longer able to cover her naked breasts, she felt completely vulnerable.

  Her computer beeped.

  “Why is my computer beeping?”

  “I loaded a web page that keeps refreshing itself every sixty seconds. It beeps every time it loads. It’s a crude way to get a repeating timer. It’s not very accurate but our game doesn’t require accuracy.”

  “What game?”

  “It’s really simple.” He began shuffling the deck of cards. “This is a standard deck of fifty-three cards. Fifty-two playing cards plus one joker.” He put the deck on the desk in front of her. “Every time the computer beeps, I turn over a card. When I turn over the joker, the game is over and I cut you loose. You’ll suffer for about an hour if the joker happens to be on the bottom of the deck. If the top card happens to be the joker you won’t suffer at all because the game will end before I turn over any of the other cards. Unless you like suffering, you should hope that the joker is near the top of the deck.”

  “What happens with the other cards?”

  “That’s the suffering part. Red cards concern your right tit and black cards are your left tit. If I turn over a red card and there is no clothespin on your right nipple, then I apply one. If there is a clothespin already there, then I remove it. Same thing with black cards and your left nipple. If you can do the probabilities, then it’s obvious that, on average, one quarter of the time you’ll have pins on both nipples, half the time on one nipple or the other, and one quarter of the time on neither. You can expect to suffer for about a half hour, though, as I say, depending on your luck that may be anywhere from zero to fifty-two minutes, uniformly distributed. Understand?”

  “Yes.” She hadn’t bothered listening to everything that he said. She gathered that he was going to put clothespins on her nipples and that would hurt. She’d find out exactly how it worked soon enough.

  “There’s another little twist.” He grinned as though he had told a joke. “Think of the cards as being numbered between one, for the ace, and thirteen for the king. The number indicates the position of application of the clothespin. From one to twelve, it will be sideways at the same angle as the numbers on a clock face. If the king turns up, representing unlucky thirteen, the clothespin will be applied sticking straight out from your chest.”

  She shrugged. She didn’t see what difference that would make.

  “Are you ready?”

  “Let’s get this over with.”

  “Do you feel lucky?”

  She looked at her arms taped to the arms of her chair and smiled bitterly at the irony of his question. If she were lucky, she wouldn’t be here at all.

  The computer beeped.

  Eli turned the first card over and showed it to her. It was the five of diamonds. “Right tit first,” he intoned and picked up a clothespin.


  He placed it gently on her nipple at the five o’clock angle, making certain that it pinched it right to the base.

  She moaned. As he slowly released the pin, her nipple began to burn. When he withdrew his hand, her nipple felt like it was on fire. It hurt like hell. She jerked and the pin bounced a little. That made it hurt even more so she concentrated on sitting as still as possible.

  The pain was beginning to fade slightly when the computer beeped again.

  The next card was the queen of hearts. Red meant her right tit got his attention again. There was already a pin there, so he gently squeezed it open to remove it.

  She had wanted her tit to be free of the clothespin but was shocked to find that releasing the pressure and letting the blood flow return hurt as much as putting it on. Maybe more.

  Two cards gone. There could be as many as fifty more cards turned over before he got down to the joker.

  The computer beeped and the next card was the ace of diamonds. Red meant her right tit again.

  Her poor right nipple was to be crushed by the clothespin again. It would hurt worse this time because it was already bruised from before.

  He attached the pin gently again when he applied it in the one o’clock position. But when he released it, the weight of the pin twisted the bruised nipple downward, making it hurt even more. She had to stifle a scream.

  Now, if she moved, the pin twisted harder as it bounced.

  Every breath was a new torture.

  After the next beep, he turned up the ace of spades. A few seconds later, her left nipple was crushed and burning just like the right.

  So it went. The pain got worse and worse as her nipples accumulated damage from the repeated crushings.

  The longest that a single nipple was crushed was seven minutes when he drew a run of seven black cards in a row. That made her left nipple hurt bad but it was less painful than having the pin on the right nipple removed and replaced in two minute cycles for those seven minutes.

  She was not lucky. The joker was almost three-quarters of the way through the deck so her torture lasted for forty-one long minutes.

  By the time he reached the joker, she was crying freely, tears flowing down both cheeks and dripping onto her suffering breasts. Her nose was clogged and running and she had to breathe through her mouth. For the last ten minutes, she had been begging for mercy and asking him to stop.

  He had ignored her.

  When the joker was finally revealed, she happened to have clothespins on both nipples. The bastard didn’t remove them, but used a pair of scissors to cut the duct tape between her forearms and the arms of the chair. Then he walked out of the room.

  She had to twist and pull her right arm to get it free of the duct tape. That jiggled her pinned nipples hard and bounced the clothespins painfully against her breasts.

  Now that he was out of the room, she permitted herself a soft scream as she released the pins from each of her nipples.

  This had definitely been worse than the paddling. Much worse.

  Her nipples were sore for two days afterward. They ached even inside her softest sports bra.

  On Friday the User Analysis Reports were emailed as usual.

  * * *

  “We only have one game left to play. Cooperate with this one and you’ll be offered the vice presidency on Tuesday for sure.”

  Keri stared at the geek for a long minute while thoughts tumbled through her mind. Concern about what “game” he might have planned was not foremost in her mind. She remembered that he had called it a “sex game” and feared that it would be something horribly humiliating but she could refuse to cooperate with him if he tried to push her too far.

  She was fretting over more important concerns than that.

  Foremost in her mind was annoyance that he kept insisting that he could assure her promotion. She was not stupid. He was not the CEO. He was not on the Board of Directors. He was a low-level computer operator. One step above the janitor. Why did he keep insisting that he had some special power over her career? It was deeply insulting that he expected her to believe that he could have anything to do with her success.

  Second in her mind was her own plan. Was he so thick that he couldn’t imagine that she had a backup plan? Apparently. That worked to her advantage because he was off guard but she had to keep reviewing her plot, looking for holes. Maybe he had been on to her all along and she had overlooked something. Maybe he was about to blow her plan sky high and she didn’t know it. Maybe he really was more cunning than her.

  It didn’t matter. Her course was set and she had to follow through to the end, be it sweet success or bitter failure.

  Finally she asked the question that he wanted. “What’s your game this time?”

  “No pain. The last game is a sex game. Come to this address at eight o’clock on Saturday night.” He pushed a paper across the desk and walked out of the room without looking back.

  He had confirmed it again. A sex game.

  She wouldn’t allow herself to be tied up for this one. She wouldn’t allow herself to be raped. Whatever she did would have to be consensual. She would make that abundantly clear.

  She’d already given one geek a blowjob. Not just a blowjob, but a world-class cocksucking. She hated to admit that she was a little proud of herself for that one. How bad could a little more sex be?

  She sat at her computer and began typing. Her list of conditions was short. No bondage. Consensual sex only. Condoms required. That was it. Three conditions. She was tempted to add a lot more but everything else was covered by the condition that she consent. As long as she reserved the right to refuse anything that was outside her limits, she would be okay.

  Eli understood that. A few minutes after she emailed her conditions to him, he was back in her office. “Your conditions are acceptable, but only as long as you are reasonable with your consent. If you refuse to have sex with anyone, then you aren’t playing the game.”

  “I’ll have sex as long as it’s reasonable sex. I won’t be raped. Rape isn’t sex, it’s assault and I won’t be assaulted. I will go to the police and file a complaint if that happens.”

  “Nobody’s going to rape you. You will be required to have sex, but under reasonable conditions and within reasonable limits.”

  “Then we won’t have a problem.” She suddenly remembered his characterization of a middle manager as someone who gets fucked in the ass by senior managers every day. “By the way, I don’t do anything anal. I can tell you up front that I won’t consent to that under any circumstance. Oral is okay. Vaginal in any position that I can manage. But no anal. That’s off the table.”

  “I can live with that.” Keri couldn’t tell if he looked disappointed or not. It was hard to read a face that never looked you in the eye.

  * * *

  The address was for an old brick row house downtown. That reassured her. If she had to scream for help, the neighbors would hear her through the walls. She doubted that it would come to that, though. Eli had been cruel, especially when he was beating her and torturing her nipples, but he had not been extreme. Nothing that he had done had been more than she could bear. Nothing had caused permanent damage.

  He might be a sadist, but he was a sane sadist.

  He had not told her what to wear so she came dressed in jeans and a sweatshirt. She had not bothered with a bra because she was pretty sure that she’d have to remove it before long and she didn’t want to have to search around for it before she left.

  When this game was over, she was going to slip her jeans, sweatshirt, and shoes back on as quickly as possible and leave without any fuss.

  “The bedroom is in the back, through the door at the end.” Eli pointed down a short hallway.

  The room contained a bed and a heavy wooden desk.

  The desk was bare except for two pillows, a box of condoms, and some kind of black leather thing.

  “What do I do now?” she asked.

  “You listen to the rules of the g
ame,” he said. “I’ve invited a few friends over for poker night. You’re the special prize. Most of the time we’ll play for chips like usual. But when I deal, we’ll be playing for your ass. You’re going to be in here, bare-ass naked, bent over the desk, legs spread, waiting for someone to come in and fuck you. On my deals, whoever wins the pot gets to come in here and do you from behind like an animal. Unless it’s me. I’m on your side, just like at work. If I win the hand, then you won’t get fucked that round. Is that okay with you?”

  “How many men?” She looked at the box. There were a dozen condoms in it.

  “Four other guys are coming over. You get to leave after I’ve dealt four times so that’s the most that you can get fucked. Four times by four different men. Odds are that it’ll be three times because I should win at least once. I’m a good player and I play to win so you might get away with getting fucked only twice. Maybe even only once. There’s the possibility that I’ll win all four hands and you walk out of here untouched, but that’s unlikely and I wouldn’t get your hopes up if I were you.”

  “I can do that.” She didn’t relish the thought of being fucked by four men, but she could do it. “One thing puzzles me, though. Why aren’t you going to fuck me when you win the hand? You don’t seem gay. You spend too much time staring at my body.”

  He smiled sadly and, maybe for the first time, looked her in the eye. “You don’t know anything about me, do you? I’ve worked for you for four years and you haven’t made the slightest effort to learn the first thing about me. This all began when you said that you were sure that I’ve never had a date in my life. Wrong. I dated lots of women when I was younger. I’ve been married for three years. I have a child, a two-year old boy, and we’re expecting a girl in the fall. I love my wife and I don’t cheat on her. Not with anyone and certainly not with the likes of you. I have standards. You’re sexy enough in a slutty kind of way, but you’re definitely not my type.”

  It was Keri’s turn to rock back in shock at his insult. She had to revise her view of Eli and his sexual history and that took some time. Then a thought struck her. “When you first made me take off my bra, you told me that you’d never seen a woman’s tits. That was why you wanted to see mine.”