Wicked Wednesday: Fuck this ladylike lady up the ass

Jennifer had asked for permission to ask me a personal question. I said, “All right, you can ask. You won’t necessarily get an answer, but you won’t get a spanking for it, either.”

“Sir? Maddie? Sir’s thing gets so big and hard when he punishes me. And when he makes me come, afterwards. But he doesn’t ask me to do anything for him. Though I’d like to. But Maddie… does sir make you please him, once I’ve gone?”

Maddie smiled. “Soon as you’ve gone, Jennifer darling. Sometimes the second after you’ve shut the door.”

“Can I please you the way Maddie does, sir?”

I placed her on her back on the couch, gently, lifted her legs and smacked her bottom. She yelped indignantly, so I smacked her again. She said, “That’s not fair! You said you wouldn’t spank me!”

“That was for one question. You asked a new question.”

She frowned, then nodded. “But?”

“No, Jennifer.”

“But… I’m eighteen! I’m allowed to choose whether or not I do sex things now. I’m legal. And I looked you up. You’re only seven years older than me.”

I nodded slowly, then smacked her bottom again. “You looked me up. To see if it was ok to have sex with me?”

“No, I just looked you up! Well, I suppose I was thinking about sex. It doesn’t feel right to me, that you give me pleasure, and I can’t do the same for you.”

“We’re not equals, Jennifer. I have to look out for you.”

“But why does that mean you can’t let me..?”

“When I punish you, little one, I do get very turned on. But I’d never punish you just for my pleasure. It’s always for your own good. That’d be true even if I didn’t enjoy it. And when I do. So, it’s the same before I let you please me. I’d have to be sure that it’d be good for you, and do you no harm.”

“But I want you, sir! I do know my own mind, and I know that! What if you’re harming me by…” She drew a breath, then blurted, “Not letting me suck your cock?”

 “You were warned about language, Jennifer. And you chose to ignore the warning. The next time you’re in this office, I’m going to spank you for that. Understood?”

“Please sir! I mean, yes of course I should be spanked for speaking like that. But I don’t know any other words! And you do so much for me, sir. How can I not want to please you?”

“You’re allowed to want me, Jennifer. In fact it makes me very happy. And you know that I want you. My cock points at you, whenever you’re in the room, and you know that.”

“You said cock! Is Maddie going to spank you for being rude? Or can I?”

“Did I say I’d spank you? I meant, strap you.” Her smile disappeared. “And I said we’re not equals. I can say what I like. It’s you that has to keep her speech ladylike.”

“Truth is, sir, I want you to fuck this lady, everywhere your cock wants me. I want you to fuck this ladylike lady up the ass. Please?”

Wicked Wednesday: Quick recovery

Maddie returned and draped a blanket over her. “Thank you, Maddie. Thank you for everything, I think. And I hope I didn’t deafen you, with all that screaming while you were holding me down. I know I bawled my head off. Even I thought I was making such a racket.”

Maddie said, “You were fine, sweet little Jennifer. You’re new to discipline, and it is a shock when you start. Though even now I sometimes find myself making more noise than that.”

“Do you? Wow.”

I put my hand on Jennifer’s bottom and squeezed her. Just enough to make her yelp. “I’m afraid I thought the sounds you made were absolutely beautiful. So are your tears, little Jennifer. Like tiny jewels on your face.”

“You enjoy punishing me, sir, don’t you? I don’t mind; you can do that as much as you like, wherever, whenever, however you like. But your … thing: it’s always so hard and big when you’re warming my poor bottom. I know I shouldn’t say that either. But I like that it pleases you.”

“You please me very much. Even when I’m not making you cry, pretty girl.”

“Heh.” She wriggled in closer to my chest. “And you like making me come, I know. That was so cool, sir, what you did when you were punishing me. Getting me ready to come, then giving me more of the slipper. That’s why it was so easy to take.”

I kissed her, and we kept our heads close to each other. Jennifer pulled the blanker round to cover both of us. I said, “Having you turned on before I slipper you helps you to get through it. You still get the same smacks, but your mind, even your body, interpret them differently. Everything feels sexy.”

“Yep. Yep, Sir. Without that I’d have screamed blue murder and tried to run out of the room.”


“Oh! I would’ve been, wouldn’t I? But getting away would be all I’d be thinking about. Instead, oh, it hurt, sir.  You made me a very sorry girl, and I promise I’m never going to flash myself at anyone. Except you, of course.”

“Of course. You’ll do as you’re told, Jennifer.”

“Oh, I will, sir. But you can’t want to see me naked again anyway. You’ve seen everything I’ve got, now. Maybe that means no more spankings for me! Ever!”

I marvelled at Jennifer, who could recover so fast from a severe punishment, and then risk more by being cheeky. She’d stayed subdued for perhaps five minutes. I hugged her, tight.

But then she was serious again. “Sir? I’ve got a question. It’s a very personal question. Can I have permission to ask it?”

Wicked Wednesday: Obedience, discipline and lotion for Jennifer

A moment later, and Jennifer was again displayed, bent over my desk, naked, her hands held tight by Maddie, in the primal submissive position for discipline or sexual use.

I pressed my sipper against the fullest part of her bottom, and delivered the first stroke, lusty and hard, almost immediately. Jennifer took that one with a grunt, but no scream.

I said, “Now, Miss Perch, it’s time you learned that when I give you an order…”

The second stroke was delivered hard and fast, and delivered to her right cheek. Jennifer waggled her bottom frantically from left to right, the pain clinging to her. She made a high-pitched sound, not a scream, but a musical note.

“I do not–“

The third smack impacted hard and hot on her left side, and Jennifer screamed.

Maddie said, “Tears now, Master.”

“Want questions or complaints from you–”

On the fourth hard stroke, on her right buttock, Jennifer screamed again, her body rocking involuntarily in that ancient dance that punished girls performed for their disciplinarians.

Maddie had to concentrate and use all her force to hold the girl down and in position.

“I want obedience.” Her bottom was a moving target now. I caught her left buttock with the slipper as it rose; the impact sound filled the room. Jennifer wailed and shouted wordlessly. She had not stopped her vocal noises since the fourth stroke.

“You will learn to do as you are told.” The sixth stroke landed across the centre of her weaving and ducking bottom, again catching it on the rise. Jennifer’s song of pain barely changed.

She was already in a world of sensation that was partly but not entirely painful, and she’d stopped reacting much to individual spanks.

I could slipper Jennifer for another hour when she was like this, and though it would raise blisters on her bottom, which I did not want, she wouldn’t really notice. It’d make little difference to her mental state.

I said, “Lotion”, to Maddie, and she passed it. I spread it across Jennifer’s bottom, while she was still rocking up and down in a parody of sexual motion. I said, very quietly, “Good girl, Jennifer, you’re done now. You’ve been very good, and good girls do get looked after.”

She made an appreciative noise as my fingers slid and stroked her. Goosebumps rose on her bottom when I let my fingertips touch her pussy. It was, I thought, time to take Jennifer’s education one step further.

Wicked Wednesday: Exercise for bad girls

When Jenny had completed her squat thrusts, naked in my office, watched by Maddie and by me, I said, “Good girl, Jennifer. You need more exercise, though, don’t you?”

She blushed. “Yes, sir. I do.”

“I’ll have a calisthenics program drawn up for you. I’m sure the coach will supervise you.”

Maddie rolled her eyes. Jerry Manderson, the coach, was notorious for his “helpful” ways with attractive students. I’d restricted his use of corporal punishment to the paddle on clothed buttocks, but he found his opportunities. He wasn’t worried about either justice or consent, let alone enthusiasm. I was going to have to fire him.

Jennifer knew Mr Manderson, and didn’t want to be under his supervision. She said, “Sir, I know that he would be best to create a program. But… could you supervise me? I could do my exercises in your office while you… I mean while you worked. I promise I’d be no bother. Sir. Please?”

I thought about that. It was a powerfully attractive offer, of course. And if I left it to Manderson he would find ways of touching her belly, her bottom and her breasts while he helped her with her exercises. Unwillingness, even revulsion, was not a problem for him.

But an intelligent girl like Jennifer could gather the evidence that allowed me to get rid of him, despite his success in coaching team sports and getting parents on his side. But I couldn’t dump that assignment on her, unless she agreed. Nor could I talk to her about staff problems. Maddie could. But I’d have to discuss it with her before I did anything. 

My silence was making Jennifer worried. Eventually I said, “Yes, for the first couple of weeks. I don’t think you’ll be needing to bring any sports clothes.”

She missed the significance of my last remark, or she didn’t mind performing for me naked. “Thank you, oh thank you, sir!”

“After that we’ll see. My office is not a gym.”

She smiled suddenly. “It seems to be an office that has many different uses, sir.”  

“Indeed. And you’ve reminded me that you still have six strokes coming.” Her face fell. “To remind you not to question orders again. Bend over the desk again, Jennifer. As you were before, bottom arched up, legs apart, arms outstretched.”

“Sir.” Jennifer turned, stepped to the desk, placed her feet well apart, and lowered herself till her belly, breasts and her left cheek rested on the table.

I picked up the slipper. “Maddie, back in position, and take Jennifer’s hands.”

Wicked Wednesday: Tears and sweat

Jennifer had just received twelve strokes of the slipper, bent naked over my desk, with Maddie holding her hands to make sure she stayed in place.

She’d been noisy and tearful through-out, and yet already, her bottom blazing red and hot, she was calm again. She had to be focussed on the hot pain across her buttocks, and finding that the heat has some quite pleasant side effects. 

I said, “”Maddie, you can let go of her hands for now. Thank you, girl. I’ll thank you properly later.”

Maddie smiled, and she stroked the backs of Jennifer’s hands comfortingly, after she’d released them. “I know you will, Master.”

“Jennifer. You’re done with your punishment, or at least the punishment for exposing yourself. Two dozen strokes over two days. Bravely taken. And now you’ve paid, and it won’t be mentioned again.”

It took Jennifer almost a minute before she could say, “Thank you, sir.” Then she added, “Thank you for punishing me. I know I was doing something wrong. It was a stupid thing to do.”

“I don’t think you’ll ever do it again, Jennifer. But if you did I’d cane you. And if there were a third offence I’d cane you naked in front of the school. I think that would cure any further exhibitionist tendencies.”

Actually I doubted that last statement, very much.

Something told me that if I ever did cane her in front of the school, she’d find a way of making sure it happened again. But I kept that thought to myself.

“All right, Jennifer. You can stand up now.”

“Oooh, yes… sir.” She raised herself stiffly and awkwardly, like an old man. But she managed to stand and face me. Indeed she had wept.

Her face was wet with tears, and her nose ran. I’d have to use many tissues if I wanted to hug her, but it wasn’t time for that yet. Anyway, Jennifer was a beautiful girl, but I’d come to love her face when she wept for me.

“We’re not quite finished for today, Jennifer, but I want to stop you from stiffening up too much. Can you do squat thrusts?”

“Yes, sir. Of course.”

“Good girl. Of course you can. Give me twenty.”

Jennifer said, “Yes, sir.” She dropped down into a squat, then shot her legs out behind her, drew them back into the squatting position, then stood up.

As she repeated this movement, I beckoned Maddie over.

She stood in front of me, eyes bright, and we hugged. She could feel my penis, hard, between the two of us. She whispered, “You’re going to use me so hard after this, aren’t you?”

“Eight, sir.”

I said, slightly louder then she’d spoken, “Yes, Maddie. You’ll stay behind, after Miss Perch has left.”

“Thirteen, sir.” Jennifer was a fit girl, but she was puffing, now.

I smacked Maddie’s bottom, and we turned to watch our girl exercise, bottom glowing, breasts bobbing. Aware of our gaze, she tried to keep the puffing inaudible. Eventually she sang out, “Twenty, sir!” She stood, arms at her side. There were beads of sweat between her breasts.

Wicked Wednesday: You may not come!

I’d told Jennifer, bent naked over my desk, to brace herself. This is always credible advice when it comes from a man with a slipper in his hand. Jennifer shivered a little, thinking I’d meant I was about to start her slippering. 

But I put my palm and finger under her pussy, and ran my thumb down between her soft, inviting folds. She jerked in surprise, and then relaxed. I put my thumb into her, feeling the spongy skin as I pressed down, moving my thumb slowly into and a little way out of her, while pressing my palm against her clitoris.

Jennifer sighed with pleasure, and then her body started to echo the movements of my thumb and palm. Her breath quickened. I admired the rise and fall of her bottom, which blushed a bright crimson from the six slipper smacks I’d already given her. But at almost the last second, when she was on the edge of orgasm, I pulled out, smacked that bottom, and said, “But don’t you dare come, girl!”

“Ahhh, sir!” She made a howl of protest, and in another mood I’d have given her extra strokes for that. 

But I ignored her. I drew her knee a little further towards me, and applied the first stroke to her inner thigh, about eight inches from her pussy. Jennifer shrieked, “Owwwwww!”

Since she could no longer kick, her body rocked from side to side on the table. I brought the slipper down again, a little harder and three inches closer to her pussy. Jennifer howled and writhed, though it was less dramatic than her response to her first six. She was getting tired, and she was transmuting at least part of the pain into pleasure. I delivered the third stroke on the plumpest part of her thigh. She yowled and then sobbed, crying like a baby.

As I crossed to her right side, Maddie said, “We have tears, Master.” I couldn’t see her face but I knew that was true, from the quality of her sobbing. I took Jennifer’s right knee, and held it firmly while I delivered the same sequence of three strokes to her right inner thigh.

Maddie still sobbed and wailed, but her body movements were calmer. Her bottom rose and fell as if her pussy was riding the air, riding something that should have been there but wasn’t. Despite her pain I knew that if I touched her she would come within about thirty seconds.

More importantly, I was now certain that she’d be able to come instantly, without my touching her, if I commanded her to.

I rested the slipper on the small of her back. “If you beg for permission to come, Jennifer, I’ll give you two dozen extra strokes. Is that understood?”

Her voice was very quiet. “Yes, sir.”

“You’re learning discipline and obedience. From now on, you come only when I give you permission.”

“Yes, sir.”

“That includes at home, in your own bed.”

“Sir! I mean, yes, sir.” 

I smiled, not that she could see me. “I know you’re a good girl, Jennifer. This is part of showing me how good you can be.”

She sighed, resigned. I’m not sure if she understood, yet, quite how much power she had just ceded.

Wicked Wednesday: Is she crying yet?

I didn’t admit any warmth or affection in my voice. Jennifer was to feel punished, before she was allowed other feelings.

I said, “Jennifer, that’s your first six for today. It’s punishment and a lesson. It’s very unwise to flash your pussy at the boys. It leads to trouble among them, and to trouble for you. I’m sure you knew that.”

There was a snuffle. “Yes, sir. I did know it was wrong.”

“So you deserve to be punished, and you need the lesson. This is to make sure your body warns you against it, if you ever even think of doing something that silly again. Is that clear?”

Jennifer coughed, twice, before trying to speak, and her voice was still small, shamed and shaky. “Yes, sir. That is so clear. God, I’ll never…” She shook her head.

That was good enough. I said, “And you’re being a good, brave girl. I’m proud of you.”

Jennifer sobbed again, relieved, then quickly controlled herself. “Thank you, sir.”

“You’ve got another six, Jennifer, for your indecent behaviour. Then you have the penalty six for questioning an order. So you’re a third of the way through. Head down, now girl. And keep your legs parted. You’re about to find out why.”

Jennifer froze for a second. She wanted to ask what I meant. But she decided better, and lowered her head again. I said, “Maddie, is she crying yet?”

“No, Master. Her eyes are wet, but she hasn’t spilled tears yet.”

I smiled, and patted Jennifer fondly on the bottom. She moaned, not with pain, and raised her hips a little further, seeking my touch. I picked up the slipper and moved to her left side.

I took her knee and pulled it a little further to the left, so she was utterly exposed. Her pussy was swollen, lips soft, and damp.

“Brace yourself, girl.”

Wicked Wednesday: Do you agree that discipline works?

Jennifer raised her head and looked at Maddie. I’d just told her that Maddie envied her, for the paddling she was getting. And, we all knew, though none of us would say it, Maddie envied her because she was the focus of desire in that room. I wanted Jennifer, powerfully. Maddie wanted Jennifer too, and to be her. 

At last, finding my words confirmed in Maddie’s age, Jennifer dropped her head to the table again. She tensed her body, then relaxed, getting herself back under control. 

But I did not want Jennifer in control of herself, even partly. I resolved that I would hear her cry out by the third stroke. I landed the second smack of the slipper hard, and on the same spot as the first. Her body jerked under the impact, and her feet left the floor, though she kept her legs spread.

Her head raised, baring her throat to Maddie, and the hiss came back, louder, and ended in a soft moan of pain.

She was fighting hard, and she was brave. Braver than she’d been under the slipper yesterday. But I was determined she’d lose that struggle, and spectacularly.

The third hard stroke on that same soft area of skin was her undoing. Her legs rose till they were almost level with the table, though she still kept them spread, and her breath expelled in a harsh, loud scream.

With the floodgates open, I stepped back a little and smacked the slipper down on the crown of her buttocks. It must have hurt less than the third stroke, but her legs kicked in the air and she screamed again, her pitch rising, perhaps a semi-tone.

Her brief resistance was gone: she was now under the slipper’s command and direction.

I landed the fifth and sixth strokes on the same spot, about thirty seconds apart, and her legs kicked and cycled in the air, ungainly as a frog’s, and the wail with which she greeted the fifth stroke had not ceased by the time I landed the sixth.

Her cries continued after I’d stopped skippering her, a very sorry girl. II touched her slipper, very lightly, against her bottom, as a warning. “Quiet, Jennifer!” Jennifer continued wailing. “Or I’ll give you another six extra strokes!”

Miraculously, she suddenly found self-control. There was just one last sob, and then silence, except for Jennifer’s hard breathing. Maddie caught my eye again, and smiled. “You’re learning that discipline really works, Jennifer. I bet Master is pleased with you.”

Jennifer shook her head. She was focussed on the raging heat in her bright red bottom, not on speaking. But Maddie reached for Jennifer’s jaw and lifted her face, so the girl and the woman stared at each other, eye to eye.

Maddie smiled. “You always find extra reserves when you’re being disciplined, Jennifer. I know that well enough by now. You’ll endure anything, and you’ll do anything if you think it will please him. Discipline works for you too, doesn’t it?”

Wicked Wednesday: Enviable girl

I met Maddie’s eyes. She was holding Jennifer’s hands tight, so she couldn’t get up. Jennifer was over my desk, face and upper body pressing onto the wood and leather of my desk, her bottom arched up and her legs splayed, feet about a metre apart. There is probably no pose or position that is more inviting, and exposed.

Maddie looked down at Jennifer’s naked body, and smiled at me. Poor Jennifer was waiting in suspense for her slippering to begin. The arch of her back, presenting her buttocks and pussy at me, was intensely sexy and beautiful. Maddie thought that Jennifer knew exactly how enticing she was, just then. I thought that Maddie was probably right.

I’d built up the suspense as long as I could. I pressed the slipper against the undercurve of Jennifer’s buttocks, to let her know where the first stroke would land. Her bottom was still a darkish red, and warm, from the hand spanking and slippering she’d received yesterday. She gave a little gasp when I raised the slipper: loss of contact could only mean that the slipper was about to come back, fast and painfully.

I held it poised over my shoulder, counting to ten. It didn’t matter that I admired Jennifer, it didn’t matter that I was becoming more than fond of her. She’d been told to ask for a merciless, hard slippering, and she’d done as she was told. She was entitled to what she’d requested.

Most girls, when told to ask for no mercy, found it necessary to obey but they also found it scary and humiliating.

Jennifer had only sounded sincere. Her mind felt she deserved it. Her body, and specifically her pussy, wanted it.

So I swept my arm down and landed the slipper hard and low across both her terracotta-red, sweetly rounded cheeks. The smack resounded, rubber against girl, as if someone had banged a leather-bound Complete Shakespeare on an oak table.

Jennifer took a second to react, then her head shot up and turned frantically from side to side, her hair flailing. Maddie’s hands, hauling Jennifer’s outstretched arms forward and down, prevented any other movement. Jennifer’s mouth opened but she fought back the scream, emitting a low, agonised hiss.

I leaned down and kissed her shoulder, and she calmed a little, though the pain of that first spank, on already-slippered skin, must still be fresh and intense.

I whispered, “Shhh, Jennifer. Even when it hurts, you know you look lovely. And we both secretly know it feels wonderful. And would you like to know a secret?” 

“Yes? Sir?” 

“Right now, Maddie is envying you.”


Wicked Wednesday: She Will Have her Way

I’d just threatened Jennifer with multiple naked, public canings, if she came before her slippering had finished.

Maddie said, “He would, too.” She was lying. So was I. But I wanted Jennifer to try her hardest.

At last, dangerously late but not too late, I withdrew my finger from her perfect pussy, getting a loud, involuntary moan of protest from Jennifer. I picked up the slipper.

“All right Jennifer. You’re having fun. But this is still punishment. You’re going to get the remaining twelve for making a display of yourself, and another six for questioning an order. It is going to hurt you, girl. It’s meant to teach you. Not just your mind; I want you to have a body memory of this.”

“Oh sir. I know I’m going to feel it, a little warning from my bottom if I even thought of being bad.”

“And yet, you’ll be back here again. Always. But never think you’re standing still. The standards for you will rise, as you learn better behavior. But I don’t think you’d ever want to be completely good, would you?”

There was silence, then she said, very quietly, “No, sir. If that’s all right with you.”

“I think that’s very all right with me.”

Jennifer raised her hips a little from the desk, so her pussy pointed directly at me. “Will you please, sir, slipper me hard and mercilessly. Oh, I’ve forgotten the words, but you know what I mean.”

 I did indeed, and my admiration for Jennifer just then had no bounds. I looked at Maddie, who knew what I must be feeling. I said, “Maddie, you make sure you hold her tight.”

“Yes, Master.” She made no attempt to correct herself to ‘Mr Beecham’. She judged that Jennifer had heard her earlier slip and made the correct inference. She looked happier, now she’d said it openly, and shared her status with Jennifer. Maddie had ways of getting what she wanted.