Punish Me, Please Me

by Ashley Zacharias

  Celine looked around as instructed. She saw the women in the room from a new perspective. Some of them would be going back to their home or motel room tonight and providing sex to the man sitting across the table from them, whether they were in the mood or not. Most of the ones that looked like they would be doing that looked happy enough. Her eye fell on one woman, a thin, middle-aged harpy who was quietly berating her husband about some shortcoming. She was no sexual slave. He already knew that he wasn’t getting lucky tonight and his shrew of a wife looked like she was the unhappiest woman in the room.

  She looked at another couple, an elderly man and a young woman with brassy hair and too heavy makeup. The woman was stroking the man’s hand gently, cooing something at him. She was wearing no wedding ring. A paid escort? His mistress? A gold digger? She looked happy and so did he. He would get lucky tonight and didn’t care what it cost. It was obvious that she was happy with her situation, too.

  She watched a third couple for a few minutes. He was in his late thirties and looked like Elvis, even down to the sideburns and sunglasses. She was at least fifteen years older than him and dressed like a business executive. They wore matching wedding rings. How did she keep a handsome young man coming home every night? Not by being an executive and writing memos to him. And not by telling him that she wasn’t in the mood so he was going to have to take a cold shower. She would act the cougar for him any time he wanted her. Did that make her a sexual slave or a great wife?

  The waiter set her steak and dry salad in front of her and set the other steak and potato in front of Paul. As soon as she left, Paul asked, politely, “Pass me your food and your silverware, please.”

  Puzzled, Celine obeyed.

  Paul pushed his own plate to one side and put her plate in front of him. Carefully, he used her steak knife and fork to trim every bit of fat from her steak – easy because, unlike his own rib eye, the bulk of the fat on a strip loin is on one side – and moved it to his bread plate. Then cut the remaining lean meat into small pieces. When he was finished, he passed her plate back to her, sans cutlery.

  “No fork?” she asked.

  “When your food is properly prepared and served, you can eat with elegance and grace without implements.”

  She delicately picked a piece of dry lettuce from the plate, put it in her mouth, and chewed slowly. With no dressing on the salad and no fat on the meat, her fingers would stay relatively dry and clean; and she had her napkin to wipe them as necessary. As subtly as she could, she slid a small cube of meat between her teeth with her naked fingers and chewed it as well. Having not eaten since breakfast and having spent a busy day, she savored the morsels of nourishment. But the lean meal would hardly sate her appetite. She would be hungry for the rest of the night.

  Paul, on the other hand, had no compunction about sawing into his own marbled steak and sour-cream-laden potato with a knife and fork. Celine got the point: the rules for the slave did not apply to the master.

  The meal ended when Paul got chocolate cake for dessert and Celine got the bill.

  When Paul returned her to her room, he packed all her clothing into the Victoria’s Secret bag and took it away, once again leaving her nude without access to a single stitch of clothing. She would not be going down to the casino to play any slots tonight. In the sexual slave’s Vegas, only one slot mattered: the one between her legs.

  Paul told her that she could rest for an hour, but that she had to prepare herself with blindfold and handcuffs for Master Exeter’s pleasure by nine o’clock. It was the first time that Paul had admitted that Exeter was here and was the one making love to her. Now she was certain that it must have been Master Exeter between her legs this afternoon.

  Sometime late in the evening, after blindfolding and cuffing herself, she was pushed to her knees to service an unseen man with her mouth, her hands being unavailable to assist. The room was silent but for her slurping and the man’s heavy breathing. She told herself, In for a penny, in for a pound, once again. I should get as much out of this experience as I can. With that mindset, she tried to imagine how a slave would enjoy servicing her master. She forced herself to explore every curve and bulge of the man’s cock and balls. She tasted every part of him, smelled every part of him, and did her best to learn how he reacted to each different variety of oral touch and caress. Being blindfolded and having her hands restrained behind her back, she was limited to judging his reaction by listening to his breathing and whimpering; and feeling him stiffen and pulse in her mouth. The experience was more educational than she expected. She always told her young students that they would get as much out of their education as they put into it. Now that she was the student, she was taking her own advice and putting as much into this fellatio lesson as she could. She was learning the truth of her own aphorism. When the man finally came, she had no choice but to swallow; with the blindfold and handcuffs, she would look foolish stumbling about the room, bumping into things, trying to find the bathroom to spit in the sink. She was sure that she had Master Exeter’s cum in her mouth and she was loathe to insult him by rejecting his jism. As the thick wad slid down her throat like a raw oyster fresh off the half shell, she suppressed her gag reflex and told herself that she wanted to please Master Exeter. If she pleased him enough, he might let her see his face.

  But not tonight. He left without removing her blindfold.

  Paul returned before midnight to unbuckle her collar and unlock her handcuffs for her. He told her that she did not have to set an alarm, if she were still asleep in the morning, he would wake her up when he came to her room.

  He said one strange thing before he left. “If you can learn to be happy serving as a slave to strangers, you will find true joy when you are enslaved to a man you love.” It was strange that he spoke the words because they were so obviously true. That was the whole point of this training session.

  She spent her remaining hour before going to bed sitting nude at the desk, recording her latest lessons in her workbook.

  * * *

  “Today you will enjoy an intensely humiliating experience,” Paul said when he entered Celine’s room in the morning. “Evacuate your bowels as best you can because we have arranged for an expert to prepare you for anal service. To keep your bowel as clear as we can, you will not be permitted to eat until after you have serviced at least one man anally. Clean yourself up, then blindfold and cuff yourself as usual. Be ready by eleven o’clock.”

  She wanted to complain about her hunger but instead, asked, “Why do I have to be blindfolded?”

  He walked over to the bed, gently raised her to a sitting position, and then slapped her face sharply. “Have you not yet learned not to ask stupid questions? You are a slow learner.” He slapped her face a second time. “Try to be a better student this morning because you have got a lot to learn about your own asshole.”

  She contemplated that she was learning about more assholes than her own, but was tired of getting her face slapped – it was both painful and humiliating – so she kept her thought to herself.

  He slapped her face a third time then left without saying another word.

  She resolved to ask no more questions and save herself at least a little unnecessary humiliation.

  Sometime after eleven o’clock, she heard her door open and someone enter. She could see nothing through her blindfold so she compensated by listening as hard as she could. She heard footsteps and the rustle of plastic. The rustling of a lot of plastic.

  Then a voice spoke. This was a deep voice that spoke with a clipped accent, not quite British, but not quite American, either. Something in between. “Cheerio, dear. They didn’t tell me your name and I have to call you something, so I’m going to call you Slut for the sake of convenience. Now, Slut, stand up and step over here.” A hand grabbed her arm firmly and guided her across the room.

  She felt her bare feet stepping from carpet onto a heavy sheet of plastic.

  “I was told that you have never experienced anal penetrat
ion before. Because this will be your first time, we will proceed slowly and carefully to make sure that it is done right. It will take considerable effort on your part but it will be worth it. Do not expect to enjoy the physical sensations at first. If you continue to receive men in your asshole, you will learn to enjoy it more. I recommend that you arrange to get your asshole fucked at least twice a week to keep yourself open and maximize your pleasure. Some women learn to experience orgasms while getting fucked in their ass and a rare few learn to prefer ass fucking to getting fucked their cunts. You may not be lucky enough to attain that lofty goal but you should reach for it. Kneel down, please.” He helped Celine to her knees. “Now spread your knees apart and push your face down against the floor. That’s right. Get that ass up in the air as high as you can and open yourself right up. Good. Very good. Just stay like that and relax.”

  It was hard to relax with her face pressed against the sticky plastic and her hands cuffed behind her back because her neck was bent at a sharp angle. The anal expert noticed because he said, “I don’t know why they cuffed your hands. You’re not going to resist me, are you?”

  “No.”

  “Good. Because I won’t do this if you are reluctant. Anal rape can do a lot of damage. If I don’t have your complete cooperation, then I’m out of here right now. Are you going to cooperate completely?”

  “Yes.”

  “Excellent. In that case, I’d like to get those handcuffs off. Do you know where the key is?”

  “It’s attached to my collar.”

  “Ah, yes. So it is. How thoughtful of them.” She felt fingers fumbling with the buckle at her neck and, a minute later, her hands were free.

  “Now,” the expert said, “You just tuck those hands under your face and give yourself a little support. That’s right. Just be sure that you don’t dislodge that blindfold. You want to keep that in place.”

  “Why?”

  “Because they told me that you have to be blindfolded for sex. It has something to do with focusing your senses, I think. Eliminating visual distractions. Master Exeter is an expert in psychology. He is a professor at a prestigious university. I don’t question his methods.”

  Celine remained silent. She was listening hard and heard a soft snapping. The anal expert was putting rubber gloves on his hands. He was serious about his work. Her gut twitched in anticipation of imminent violation. A few moments later, she felt a cold slimy finger rubbing around her rectum.

  “Always use lots of lubricant. Your cunt can make it’s own slime. When you’re excited, your cunt can literally be dripping inside. But your asshole has no way to lubricate itself, so you have to do to job manually. Water-based lubricants like K-Y jelly have to be used immediately because they dry out after a few minutes. Petroleum-based lubricants can last all afternoon but they can damage latex and render condoms useless. You want to make sure that strangers use the love gloves in your back door because you can get diseases there more easily there than from any other kind of sex. There’s always a little abrasion with anal penetration that lets the viruses right in. If you know that your lover is clean, though, sexual etiquette dictates that using a condom is his option. You can’t get pregnant back here. Personally, I always use a condom because I hate getting urinary tract infections.”

  All the time that he was talking, Celine felt him working more lube deeper into her. After a minute, he added his middle finger to his index so that he was using two fingers to penetrate her. She felt herself being stretched open. It was not comfortable, but it did not exactly hurt, either. “The other advantage of a condom is that the man can strip it off if he wants to switch to your cunt. Don’t let a man ride your asshole bareback and then switch to your cunt without washing himself off first. You don’t need the bacteria in your vagina. You have a duty to keep yourself as healthy as possible for your master’s enjoyment. There we go,” he said, “I’ve worked a goodly amount of Astroglide into you. Now we’re going to try a little real penetration.”

  She heard a case snap open. “This is a small anal plug. It’s not much bigger than my two fingers and softer, so it should slide right in.” She felt the pressure of an object against her anus. “You’re still a little open from my digital stimulation, the anus doesn’t close all the way immediately after being forced open and you can use that fact to ease the penetration of larger objects. Oops. There it goes. How does that feel?”

  Having an alien object stuck in her anus felt strange. “It feels odd.”

  “Does it hurt?”

  “No. Not at all. It just feels strange.”

  “That’s to be expected. You have bigger things than that passing out every day. But they move along, they don’t stick halfway and keep holding your asshole open.”

  Celine felt her sphincter muscles twitch and the object popped out of her. It hit the plastic between her knees with a quiet thud.

  “Ha. See. That’s your natural reflex. You’d be surprised how hard it is to keep even a the largest dildo stuck in your ass unless it’s strapped in place. There are women who could keep this little one inside them indefinitely but that’s a skill that requires an awful lot of practice. Rather than putting this little thing back in, let’s move on to something bigger.”

  She felt his fingers smearing more lubricant around her anus. “More lube never hurts and too little can be a problem, so take every opportunity you can to grease your asshole. Now, let’s see if you can take this.” She felt another cold object pressing against her outer sphincter. “I’m not going to push it in. I’m going to hold it steady and I want you to rock back and forth and do the work. That’s right. You’re going to have to force it a little, but not to the point of pain. Push on it and then move away and come back to push again. Try to get it a little deeper each time. It’ll happen naturally if you just keep pushing to the threshold of pain and then backing off. There’s a trick that you will learn to use here. As you’re pushing against it, try to expel it like you’re taking a shit. See, when you defecate, you tighten your bowel but, at the same time, you automatically relax your sphincters to let the bolus out. If you do that now, you’ll feel like you’re trying to expel the dildo, but you’re actually relaxing the gate and letting the intruder in. There you go. Exactly. It’s in right up to the base. How does that feel?”

  “It’s a kind of relief to have it in finally.”

  “Sure it is. Think of it this way. It feels great to take a big dump, right?”

  “Right.”

  “Well this gives you that great feeling of taking a big dump, but it doesn’t end. It just goes on and on.”

  “It kind of hurts.”

  “Sure it does. Your sphincter doesn’t like being held wide open like this and it’s going to complain about it. But it’s not the kind of pain that means that you are being damaged. It’s the kind of pain that means that you are experiencing something out of the ordinary. Now I want you to just stay as relaxed as you can and see how long you can keep this dildo stuck up your ass. If you feel it slipping out, then you can reach back and push it back in. But try to keep it in without holding it all the time. You want to teach your muscles to relax and not work against you all the time.”

  She heard more rustling of plastic. The dildo kept threatening to slip out. She had to reach back and push it back in deeper almost constantly.

  “Okay,” the bass, clipped voice came back to her. “Now you just hold that in place while you stand up and waddle over here.”

  She reached between her legs, pushed against the base of the dildo and stumbled to her feet. The man’s strong hand around her upper arm helped her keep her balance while she was standing up. As he suggested, she could only waddle when she was hunched over keeping her hand between her legs while being guided across the room.

  “Now keep that dildo in and sit down.”

  She felt the desk chair against the back of her knees and lowered herself down. She moved her fingers out of the way to allow the seat of the chair to push against the e
nd of the dildo. The same stiff plastic that had covered the patch of carpet also covered the seat of the chair. The anal expert came well-equipped with rubber and plastic.

  “We’re going to let your asshole stretch out for a while. I guess I ought to keep temptation away from you. Put your hands behind your back, please.”

  She meekly put her hands together behind the back of the chair and let him snap the cuffs around her wrists.

  “And we better make sure you stay in place.”

  She felt soft rope wrap around her waist and upper thighs tying her firmly to the chair. When he was finished, she could not raise herself from the chair or expel the dildo no matter how she tried.

  “I think an hour is what the doctor should prescribe. That’ll give your asshole time to adapt nicely to the penetration. Think happy thoughts, Slut.”

  She heard more rustling of plastic, then water running in the bathroom, and, finally, the door open and shut. She had been left alone in her room, naked, blindfolded, tied to a chair, a dildo forced up her butt. She hoped that the anal expert had hung the “Do Not Disturb” sign on the doorknob. She’d hate to have the maid come in to make up her room.

  Not that it required making up, she’d made her bed herself as soon as she had got up this morning. She didn’t want to have to endure another paddling. Unlike public school, Master Exeter’s private lessons permitted corporal punishment and she had no desire to feel the paddle again.