Wicked Wednesday: Maddie’s orgasm

Maddie said nothing. She could enjoy whatever was to come, but what happened or how it happened was not her concern. I put lube, more that seemed possible, on my condommed cock, then put my hands on her ass and opened her a little. The moment she knew she was to be taken anally was the moment my cock pressed against her little ring.

She said, “O”, teeth still holding the cane. I pushed forward into her, slowly but in one long movement. Maddie didn’t breathe. I stopped, then, my belly tight against her buttocks, my cock throbbing deep inside her. My body was shaking with the pleasure of it. 

I’d intended to fuck her hard and fast, refusing her permission to come, but something in her acquiescence called to me.

She was submitting deeply. She was being a good girl. So I fucked her ass hard, but less brutally than I’d planned. Maddie rolled her hips with my movements, holding my cock tight, keeping me deep inside her.

Her breath sped up, after we’d rocked together for some time, and so I sped up too, pumping her hard and feeling my orgasm collecting, building, at the base of my spine.

I reached under her to stroke her cunt, and we moved hard, bodies joined, until she came, squealing and yowling like a fucked cat.

I said, “good girl, good girl,” over and over, while she came. It was the first time I’d praised her since this morning, though she’d worked all day to obey and please me.

Later I dragged out the spare matters from the sick room, and we piled up sheets and [illows and lay together, a girl and her master.

Companionably. 

 

 

Wicked Wednesday: Maddie trembles

Note: 

This was intended to follow the prompt, Recollection. Unfortunately, the story grew before the recollection part came up. So I’ll have to use this week’s prompt next week. Or, knowing me, it might be the week after. I’m slow. Sorry!

Jennifer’s pleats and pleas: Maddie trembles

Maddie returned, sinuous on all fours, with her panties in her teeth. She stopped at my feet, so the cane was beside her again. She straightened her back, remaining on her knees, and said, “‘Ay ‘anties, sir.”

I took them from her mouth, without speaking. Or smiling. She wanted the tension broken, and at the same time she’d have been horrified if it were. So I said, “You pick up that cane, and hold it out in front of you. Palms up. You’re not to grip it.”

“Yes, sir.” She took the cane and held it as I’d instructed, offering it, and of course herself, for me.

She knew I’d come back from my encounter with Jennifer highly aroused, and that I was going to take her far, as well as hard. We were going to be dramatic. 

I crossed over to the neatly stacked shelves. “Tidy means ‘clean’, girl. Do you think these shelves are clean?”

“Sir, please, I did my best.” It wasn’t like Maddie to beg. But she knew she’d lost any chance of influencing what was going to happen to her, and she was a little unnerved.

I rubbed her panties, white and lacey, on the upper surface of the top shelf. She watched me, like a trapped bird watching a cat. I said, without looking at the panties, “Because if that shelf is not absolutely clean, I should take that as an insult, shouldn’t I?”

She froze, stricken. There was no safe answer to that. Eventually she said, “I’d never want to insult you, sir.”

I held her panties in front of her eyes. There was, fortunately, a reasonable collection of dust there. “Don’t even try, girl, to say you think that’s acceptable.”

“No sir. Oh, sir, I’m so sorry!” Somewhere, she knew this was theatre, designed to ramp up her reactions, and to express my needs. But that part of her that knew that was no longer in control.For now she knew only that the man she’d surrendered to was going to punish her, and that events were happening too fast for her to even think about how to influence what happened. Her palms, holding out the cane, were trembling. 

I said, “Stand up.” This was hard, with her hands still stretched out in front of her, but she managed.

I took the cane from her at last, and said, “Now turn around. Bend over and touch your toes.”

“Yes, sir. Do I count the strokes aloud?”

“Count and thank.”

I caned her hard, poor girl, letting the stripes form from the crown of her bottom to about three inches down her thighs. And I took my time, letting her feel each one, while I watched her tremble and fight for control.

She stayed down throughout, keeping her fingers in contact with her toes. When the count got to “13, thank you, sir”, I paused.

The was a tremor in Maddie’s voice, and I liked hearing it. I’d intended to give her more strokes, but her well striped ass and trembling thighs called me, urgently.

I put the cane in her mouth, unzipped, letting my pants fall to the floor, and took condom and lube from my coat pocket.

 

 

Wicked Wednesday: Maddy’s tears

Maddie waited naked, her hastily discarded dress on the floor beside her, facing my door, on her knees. She’d heard the scene with Jennifer, and she well knew the mood I’d be in. I put the cane on the floor beside her. She knew that wasn’t because I wouldn’t be needing it, but so she could pass it to me when it was time.

I saw that she’d tidied the storeroom beyond any reasonable complaint. There were neat piles of papers, clearly labelled, tidied rows of books, and the boxes made neat stacks on the upper shelves.

When I looked back at Maddie she’d opened her mouth and put her tongue forward, covering her lower teeth and pushing out her lip. The invitation was almost irresistible. She wanted, as she always did, to direct what happened. I stepped forward and slapped her face with my left hand. Her head jolted the the right, then to the left when I repeated the slap, backhanded. 

They didn’t need to be hard slaps, and they weren’t. Their psychological effect on Maddie was what counted. They dropped her, instantly, into submission and a world in which she had no influence on what happened. It was only necessary for her to serve. I grabbed her hair then, unzipped and thrust hard into her mouth, filling her before she had time to gasp for breath. 

She sucked me, running her tongue under my cock, keeping her eyes on mine, as she’d been told. I savoured her warm, wet harbour, and counted to ten. That was as long as she usually took to start worrying about choking. Her eyes showed worry at twelve seconds. I counted slowly to fifteen. 

It wasn’t that she couldn’t hold her breathe; she could manage over a minute. It was that this was the ultimate loss of control for Maddie, and she feared it and desired it at the same time. At eighteen I pulled her, fast, off my cock, and she gasped for air. 

The tears ran down her cheeks, making runnels in her mascara while she fought for air, my cock poised in her mouth for the next thrust.

Then there was no more air, only cock.I pushed against the back of her throat.

Maddie stiffened and fought for control. Eventually she relaxed, and put her hands on my shins, not for support but for affection, while nearly twenty seconds passed. So I withdrew a little, and allowed her the comfort of having her mouth rather than her throat fucked. She sucked and tongued diligently. 

I watched her eyes while hers watched mine. She was happy. And she expected me to come soon. 

Reluctantly, and with seconds to spare, I withdrew from her mouth. I wanted to tell her she was a good girl and had pleased me, and she plainly needed that.

But it would break the mood. I said, “You think this is tidy, Maddie?”

She frowned. “Well, yes, Sir. I thought so.” 

“Well, we’ll see. Your panties are in your desk, I assume?” She’d shed them when I’d had her this morning. She knew I’d disapprove, painfully, if she’d put them back on. 

She nodded. “Yes, Sir.” 

“Fetch.” 

Maddie put her hands on the floor, and crawled to her office.

She knew better than to stand up.

Wicked Wednesday: Beautiful, bell-like, orgasm

I dipped my finger in the oil collected at her anus. “Hmm,” I said. “I’m sure you’ll often find this part of your body lubricated in the future.” 

“Sir?” 

“A man who wants you, Jennifer, will certainly need to take you here.” I pressed my finger down a little, not quite entering but letting her feel her own muscles ready to admit me. Then I spread the oil, moving down into her perineum. Jennifer’s moan was loud, and unambiguously sexual. She was nearly ready.

“But that’s in your future, girl. For now-” 

I resumed stroking her buttocks and thighs, with Jennifer rising and falling under my hands. Her breathing was urgent. She was close. 

At the last second, I reached low on her buttocks and pressed hard, fingers digging into where her sciatic nerves would be. Jennifer sobbed, once, and her body rose briefly from my table. She was silent after that, trying to conceal that deep and perhaps surprising orgasm she’d just had.

I maintained the pressure, and a few seconds later she gave another shudder, and then was still. Her face looked anguished. Her eyes were wet. There were tears on my desk.

I resisted the urge to take her in my arms, kiss her and praise her, and instead resumed kneading her as if nothing had happened. My cock ached, in restrictive clothing. I wanted her so powerfully. 

After a minute I slowed and stopped, and gave her right buttock a pat. “I think that’ll do you, little Jennifer. I’m sure we’ve dealt with any pain.” 

There was no response. Jennifer was still entranced. There was drool as well as tears on my desk. I reached for her shoulder. “Girl.” There were threats, disciplinary threats, in my voice.

She let me help her up. She stood, panties still round her knees, and looked at me, red-faced, wet-eyed. She wiped her mouth. She wore no lipstick. Suddenly she launched herself, threw her arms around my back and kissed me. It was passionate, needy. I was sure it was the first time she’d kissed a man.

I let the kiss last, because it was wonderful and I wanted to treasure it, and it meant she had surrendered to me more than she knew. Yet. She rubbed her breasts against my chest. “Thank you, sir, thank you, thank you!” 

But eventually I smacked her bottom. She remembered where she was. She stepped back. “Sorry, Headmaster. I was – I just wanted to say thank you.” 

Of course I smiled. “You are an incredibly good girl, Jennifer. And sweet-natured. And there’s nothing at all wrong with that.” I spoke with absolute sincerity. These things were true. “Now, the oil’s soaked into your skin, girl, so you can pull your panties up now.”

For some female reason she turned her back for this operation, so that I could watch the slow concealment of the lower half of her bottom. 

When she turned to face me, a smiling girl, her face only slightly flushed, I gave her a piece of paper I’d had Maddie type earlier. She looked at it blankly. “Sir?” 

“That’s a note to Wynetts. The shop your mother bought your uniform. Take that piece of paper to them – they’re expecting you this afternoon – and try on uniforms till you find one you’re comfortable in.” 

“Sir, please. I can’t take-” 

“There’s a school fund for exactly this sort of issue, Jennifer. You can and you will. Get s uniform that looks good. Not like the one you’re wearing now, and not too conspicuously modest either. Just get something so that you look like the other girls. All right?” 

She stepped towards me, then stopped. Propriety had broken out. She said, “I’m glad I kissed you, Sir.” 

I smiled. “Do you want your bottom smacked again?” 

Her face was pure mischief. “Perhaps.” 

So I tried to look stern, and said, “That’s enough of that.” But I couldn’t stop smiling. I took her ear and led her to the door. “Off you go, Jennifer. See me tomorrow morning, in your new uniform.” 

“Yes, Sir.” I resisted the urge to pat her bottom, and shut the door behind her. I sighed, happily. I need release. I needed Maddie, with some urgency. After some thought, I took the senior cane from my cupboard. I had no idea if she’d properly tidied and cleaned the storeroom, and I’d warned of consequences if she hadn’t. She’d be waiting for me, having listened to, among other things, Jennifer’s beautiful, bell-like orgasm. 

I opened the storeroom door. 

Wicked Wednesday: Rubbing it in

I gazed, awed, at the pink blush of Jennifer’s bottom and thighs. She was still red in the spots I’d concentrated the spanks: the centre of her buttocks and the tops of her thighs.

I took the oil and poured a little trickle onto the upper cleft of her buttocks, where she would be autely aware of the trickle running slowly down, some collecting at her anus, and some trickling lower.

She would want me to rescue her from that trickle when it reached her anus, certainly her cunt. She would want me to touch her.

As if having the same thought, she expelled her breath and moved her feet slightly apart, exposing her pretty, swollen and – I was sure – achingly wet and needy pussy. There was silence for a moment. Tribute not just to the sexual power of our situation, but also to her sheer beauty.

“That’s good, girl, that’s lovely. Your behaviour, I mean.”

“Thank you, sir.” She knew what I’d meant.

I poured a generous helping of oil onto my left hand, put the bottle down and rubbed my hands gently together. I rubbed her bottom gently until most of her bottom and thighs were slippery and shining.

Then I used more force, pressing my thumbs into the centre of her gluteal muscles. Jennifer made a little squeal of relief and pleasure, as I worked on the knots of tension in that gloriously firm and round ball of muscles.

Her upper body flattened entirely onto the desk and her ass rose, surrendering herself entirely to anything I might choose to do with her. Her head was turned so her left cheek rested on the wood. She was smiling, lips slightly parted, and her eyes shone.

I worked my way down to her parted thighs, finding and working on any knots of tension until they were gone. She made little pleasure noises as she relaxed, and I knew those would be the noises I would hear when her need and her nerve had build up to the point where she begged me to fuck her, and I decided she was ready. I resolved to hold off for at least a fortnight, no matter how prettily she begged.

The knots dealt with, I was gentler and more sensual as I stroked and pressed her thighs and bottom on the return. I wanted her to feel, just from my hands, how tender and beautiful I thought she was. She sighed, lost in pleasure, and her left foot again moved a little further to the left.

The trickle of oil running down her cleft had nearly reached her anus. I was sure that she was very aware of the oil’s slow encroachment.

I ignored it, and continued her massage, clasping and kneading her soft, now utterly relaxed, flesh. Jennifer’s sighs and other sounds were more overtly sexual, a young woman being pleasured, and her hips started to move, gently up and down as if being fucked by an invisible lover. Every breath she took was audible now. She was absorbed, and lost. Nothing existed except for my hands, I guessed.

She stilled suddenly. The trickle had reached her anus. “Sir?”

I pulled her cheeks apart, though it wasn’t strictly necessary.

Wicked Wednesday: Jennifer considers “feeling better”

“What do you mean, ‘feel better’? Sir?”

I put my hand on her cotton-cocooned right buttock and squeezed, to remind her that there was nothing to stop her from getting her morning spanking all over again. Jennifer shivered, her soft skin and firm muscles trembling under my hand. She understood that I was threatening to repeat her spanking. But she liked my hand.

 “Some people get spanked regularly and often, Jennifer-” She made a wordless noise, not of protest but of recognition. Jennifer had learned that that was the kind of girl she was. “That’s the world you’re in now. Now, girls like you often need aftercare. And if they’re been good after their spanking they should get what they need. Does that sound sensible, Jennifer?”

There was a pause. She was looking for the trap. But it was hiding in plain sight. Eventually she said, “No, that does sound reasonable, sir.”

“Now, Jennifer. You’ve got a sore bottom, but you’ve been a good girl all day, I’m told. So you can have something that can take the pain away.”

“Sir?” She sounded shocked. Her imagination was, of course, running wild. She was seconds away either from protesting or making some declaration of consent or need. The latter was more likely but I didn’t want her to do that today. She needed more time, to build up a deep and desperate need before I’d let her consent.

“It’s a natural oil mixture, with aloe vera, lavender, arnica and cocoanut oil for vitamin E. It cools the spanked area and takes away most of the pain, and sets about healing the skin. To let you sleep easy, and, well, let you sit down again without it being awkward. It’s for girls who get into trouble a lot but they’re good girls really. Would you like that?”

Nude young woman applying lotion to her bottom

There was a longer pause. Jennifer knew she wouldn’t be applying the mixture herself. That left strong, male hands kneading her flesh, healing the skin I’d hurt earlier that day.

I suspected that would appeal in its own right, and anyway it’d be better than going home with a sore bottom.

Finally and bravely Jennifer said, “Yes, I’d like that. You mean like a massage. I like those.”

I collected the tube of oils from the corner of my desk, where it lived with the pens pencils and felt tips and paperclips. I put a dab on the lowest vertebrae in the small of her back. A subdued, noctural animal sound from Jennifer. She was so needy, so aroused.

I put my fingers in the upper hem of her panties, and pulled them, not down, but away from her skin, revealing a perfect bottom, unlikely to be quite as sore as she’d claimed but still prettily pink from her spanking.

Jennifer groaned. “Oh sir, please. Can you leave my panties up?”

“Have I already seen your bottom, Jennifer? Quite recently?”

“Um. Well, yes, sir. You did. You have.”

“So is it something about your panties, then? Have you got a laptop hidden down there?”

She laughed. “No, sir.”

“So you’re fussing, girl. All right, you can help me. You take them down for me. All the way to your knees, please.”

“Thank you, sir.” Jennifer reached back obediently. The panties came down, slowly, as if she felt it was a gift that should be savoured inch by inch. She pulled the bunched cotton past the fleshiest part of her bottom and tugged them all the way down as instructed.

She was a spanked angel, smelling of musk and almond flour, half naked over my desk.

 

Wicked Wednesday: Jennifer and the desk

I watched Jennifer’s face while she thought about removing all of her clothes for her twelve strokes of the cane. She frowned, staring at the carpet in front of my desk. Then down at the desk, which she’d probably be bent over while I caned her. Then she looked at me.

Her face was calm, now. She’d assimilated it. If I thought it was necessary, then she’d be a good girl, for me. Or maybe it wasn’t about being good. That spanking had brought her close to orgasm. Maybe she was thinking of how she might feel, undressing at my command while I watched her, till she was fully exposed and about to receive that fiercer sting to her body. I wondered how long it would take her to make sure it happened. 

I interrupted her thoughts. “So, you’d best bear that in mind, girl. But I wasn’t just talking about discipline for you, though you do need that. Don’t you?”

She looked down, then, her face still hanging, looked up at me through her lashes. She was a natural coquette. “Yes.”

I let my voice be harsh. “What do you need, Jennifer?”

“I need discipline, sir. Sorry, sir.”

“I’m glad we agree. Now, I know that this uniform has given you a reputation, and it’s not one that’s good for you. It’s affected your behaviour already. and if you keep wearing it, it will affect those marks you’re so proud of.”

She looked confused for a second, then nodded. Oh, I meant her school marks. I was sure she’d looked at the marks of her spanking in the toilets, and rubbed them well. I wondered if she’d had that orgasm she’d been so close to, over my knee. “I think you’re right, sir. I wasn’t -” But it was too complicated. She shook her head.

“I know, Jennifer. It wasn’t so good for you. Now, I have a solution, that should help you concentrate on your schoolwork from now on.”

She looked expectant, and sure she was out of trouble now. So I pushed my chair a little way back from my desk.

“But we’ll talk about that shortly. For now we have some other things to consider. First, Jennifer, I made you an offer this morning. For extra tuition, and extra discipline. Have you been thinking about that?”

“Yes, sir! And -”

I held my hand up. “Not now, Jennifer. I said you had a couple of days. I don’t want to hear a rash decision from you. But I’m pleased you’ve begun thinking about it. I want you to think it over, very thoroughly.”

Her face fell. She’d been on the brink of telling me she’d accepted. Then she’d have made sir happy with her. And an adventure would start. “Now, Jennifer, step forward.”

“Sir.” She did as she was told, some of her wariness returning. “Now girl, bend over my desk.”

“Sir?” 

“Don’t pretend you didn’t hear me, girl. I have little patience for games like that.” 

“Sir? Have I -” 

“It was an order, Jennifer. You obey orders. You don’t question them.”

Her mouth dropped again. Had the adventure begun? She put her hands on the desk, palms flat. She looked at me. Her expression was solemn. This was an important moment.

Her palms slid forward as she bent neatly at the waist, and lowered herself into that most basic and uncompromising of punishment positions.

The skirt rose as she lowered her body, 

Wicked Wednesday: The return of Jennifer!

I should have had more faith in Maddie. The message that Jennifer Perch was to report back to the headmaster’s office, immediately after her last class, went over the PA system just before the lunch break.

That gave her fellow pupils an hour to tease her about how she must really be in trouble this time. And the rest of the school day trying to concentrate on her work while she worried about what was in store for her, when she entered my office for the second time.

So she was pale, and her voice trembled when she stood in front of my desk. She was acutely self-conscious. She’d give anything not to be here. But she said, “You wanted to see me, sir.”

I looked at her, unsmiling, saying nothing, until her bare knees shook. She was fighting back tears, certain she was about to be spanked again. Or worse.

Finally I said, “Your uniform.”

“Yes sir?”

“Jennifer, you’re out of uniform. In school hours. That’s a serious offence. The school regulations clearly state that the uniform will be appropriately fitted. Yours is at least two sizes too small.”

Jennifer blushed furiously. “I know, sir. But my mother bought it without me. And when I put it on, and found it was too small, the shop wouldn’t take it back. My mother had already ironed it. There’s a … well, you can see where she she’d set the iron too hot, when she started. But … but she said she’d talked to you, and that you’d said it would be ok.”

She sounded almost frantic now. She’d realized that she couldn’t be sure that her mother had told her the truth. She watched me like a rabbit watches an approaching dog.

I still hadn’t smiled. “Yes, she did. And I did agree. But that, Jennifer, was before I understood that you were taking advantage of your uniform to make an indecent display of yourself. Yes?”

Jennifer thought. I meant before school this morning, how she’d displayed herself for the boysl. The tears spilled at last, and she hung her head. “Yes, sir.”

“Look at me, Jennifer.” She did, and I finally smiled at her. She took a deep breath and gulped, and some of the tension left her face and body. “And we dealt with that this morning. Thoroughly, I think?” I looked at her. After a second or two she smiled.

“Yes, sir.” Her bottom would have recovered by now, and the memory of her spanking was not entirely unpleasant. More embarrassing than painful, and some of her feelings had had nothing to do with embarrassment. Her thighs had trembled, slightly parted, while she’d hovered on the brink of orgasm.

And the thought of her experience made her smile. We shared a moment of complicity.

“Well, Jennifer, I haven’t called you back to re-visit that incident. I’m more interested in making sure it doesn’t happen again.”

“Sir?”

“Jennifer, you know that this morning you were playing up to the expectations that had been created for you by that uniform. You were being teased, and boys couldn’t take their eyes off you. Your immodest display was your way of dealing with that. Or trying to take control of it. Yes?”

“I suppose, sir.”

“I don’t think it’s naturally you. And the way you tried to deal with it didn’t turn out so well, did it?”

The flush was back. That bare-bottomed spanking over my knee. It was never far away. “I – I suppose it didn’t, sir.”

“I don’t just mean your spanking, girl. That put a stop to it. Or it better have.” She nodded fervently. “If that happens again, I’ll cane you, Jennifer. Twelve of the best. Understand?”

She put her right foot over her left foot so she stood cross-legged before me. “I do, sir.”

“You possibly heard that I had to paddle two girls from your class yesterday. Yes?”

“Yes, sir.”

“You know what they were wearing when I’d finished with them?”

“No. They haven’t talked about it. Not to me, anyway.”

“Well. I can see that they wouldn’t want it known.”

I was giving her a powerful gift, of course. In her class, and in her circle, gossip is power. “The pair of them were wearing red paddle marks across their bottoms. Nothing else. Nothing at all.”

“Oh.” Jennifer was wide-eyed.

She swore that she wouldn’t need to be caned. But we both knew that was nonsense

“I am authorised to specify what pupils will wear while they’re being punished, Jennifer. Now, if I have to give you those twelve strokes, Jennifer -“

“You won’t! Sir, I promise you won’t!”

“Well, we’ll see. But you see how what those two silly girls were wearing will apply to you?”

Her mouth dropped open.

“You won’t be worrying about uniforms, if you earn yourself a dose of the cane, Jennifer. Twelve strokes. Naked.”  

“Oh sir!” Oddly, I had no idea what she meant by that.

Wicked Wednesday 240: Jennifer’s pleats and pleas 13: A fresh slate?

Maddie had asked me if she could suck my cock. It was true that she enjoyed giving head, and under some circumstances she could come from it. More or less. Actually she could come if she could find something she could press her pussy against, like her ankle, in some positions, or my leg. Still, she certainly enjoyed it, and was rightly proud of being good at it. 

A good girl: Maddie at 4.30, Version 1

But this time she’d probably offered because she was worried I was annoyed with her for being free with her advice, and for the shambolic condition of the photocopy room. And I had the cane in my hand.

So she  hoped that her lips around my cock would distract me from giving her more of that cane.

But I’d fucked her only a few minutes earlier. Probably I would get hard once she took me in her mouth, and even come, because she really was skilled and enthusiastic. But the urge was no longer urgent. And I knew it’d be an urgent need later today. 

So I stepped back and zipped up, while she watched warily. “No.” 

“As you wish, sir.” Maddie sounded dismayed. She watched, with alarm, the hand that held the cane. 

Erwin Schrödinger: famous for thought-experiments involving pussies

“Get Jennifer into my office after school, giving me a good reason to have called her. And have this room tidy and spotless. If you do both of those things, to my satisfaction, then you can suck me off.” 

She nodded. “Thank you, sir.”

“Stand up.”

Maddie stood, her skirt still around her hips. I smacked her pussy, hard, with my hand. She grunted with the impact of my palm on her most sensitive skin.

Her eyes seemed to glaze. I liked the feel of her pussy against my hand while I hurt her, so I smacked her again. And again, while Maddie kept herself open, and still. Then I smacked her left inner thigh, hard, and she spread her legs wider for me. I put the cane against her labia. “Step forward.”

“Sir.” Maddie obeyed, so that the cane, where it had been touching her, disappeared between her lips. There was both excitement and fear in her eyes. She wanted to ride it, press the bamboo deeper into her and slide wetly back and forth on it, but she didn’t dare.

I nodded at her. I’m not sure if she saw me. All her attention was focused on her pussy, and the effort to keep still. I said, “Fail at either task, and what do you think happens instead?”

A bad girl: Maddie at 4.30PM, version 2

She shook her head, trying to concentrate. “I’d have to undress and bend over your desk. And you’d cane me. Sir.” You could hear it in her voice: I was a monster.

“We’ll discuss your recent behaviour, yes. For a very long, painful time, Maddie.”

She nodded. She knew that was true.

“And when we’re dome you’ll find driving home very uncomfortable. And you’ll be standing up or lying on your tummy for the next few days. That’s a guarantee.”

Maddie looked at my shoes. “Sir.”

I took the cane away from her pussy, and smacked the top of her right thigh. Then I held it so she could hold the middle. “This has got you all over it. Clean it, and put it away.”

“Yes sir.”

“I hope I do have to cane you, Maddie. It wipes the slate clean. It’s always a new start for you, whenever you’ve been punished.”

“That’s true, sir. I hope Jennifer comes to learn that.”

 I stepped back. “Right. We’re done for now. You may leave.”

“Thank you, sir.” She stood and tucked her top back into her skirt. She retrieved her panties from beside the photocopier and lifted her foot to put them on.

“No. Put them in your drawer. However today ends, you won’t be needing those.”

Maddie blushed. That meant she expected to pass both tests. If she’d expected to get the cane instead of the cock, she’d have paled.

I knew she was happy as things were, so I resisted the urge to smack her bare bottom fondly, or to say something approving or reassuring to her. I turned without a word and walked through the door into my office.

 

Wicked Wednesday: Jennifer’s pleats and pleas 12: She’ll be coming when she comes

Maddie was on her knees before me, skirt round her waist and her panties on the floor near the photocopier. She had her hands on my shoes, the taste of my come in her mouth, and a fresh, vertical cane stroke running down her left buttock. 

And she had a plan to tell me. She said, “You know Jennifer wants to give herself to you.”

“Let’s not get ahead of ourselves.”

“It’s silly to pretend you don’t know that. She wants you to take her under your wing. She wants to be disciplined, so long as it’s by you, and she wants you to steer her to achieve what she’s capable of. And she wants you to steer her sexually. Learn from you, but also give you pleasure.”

“You know this just by listening to her getting spanked?”

“I know where she is, sir. I was a girl like her, once. Come of age, but no idea what to do. I was doing a lot of acting out, sexually. But I wanted an adult man to teach me. Not schoolboys. So does she. She nearly came when she was over your knee. And she was giddy afterwards. Happy. Wanting you. God, the things that men don’t notice.”

I knew that Maddie was talking about herself at 18 as much as she was talking about Jennifer. Still, calling me obtuse, and her earlier use of the word ‘silly’, had pushed her over the line. I raised the cane and brought it down on her pale and round right cheek. “Ahhh!”

She wriggled and breathed through the pain, keeping her eyes on mine, the way she did when she sucked my cock. Because she was watching, I raised the cane again, and – when the alarm was clear in her eyes – slashed it down again, onto the reddening, slightly raised trail of the previous stroke.

Maddie waggled her delicious bottom harder, like a duck leaving the water, fighting to stay in her position while the pain ran through her. “Ahhh-Hooo! Oh, sir!” 

“Insolence, Maddie. Try to keep it to a minimum. Even when you’re telling me what you think I should do.”

“Thank you, sir. I’m sorry. I meant no disrespect, sir. First, I think you need to let her wait for a bit, and want you. She’ll give you a reason to punish her again soon. She’ll make sure of that. But let her wait till she’s feeling brave, and horny, again. It won’t be long.”

“All right.”

Who doesn’t enjoy aftercare?

“And when she does misbehave, you should punish her, certainly. Over your knee. Nice and slow. Let her enjoy herself. But this time you should let her come.”

“And then punish her for being a filthy girl?”

“You may, sir, but I hope you don’t. I hope you pretend not to notice, to spare her any embarrassment. But you should give her a lot of affection afterwards.”

“Rub her. Kiss her. Stroke her. Praise her?”

“Absolutely. A lot. She’ll need it. She’ll be dazed. It’ll be her first orgasm with a man. It should be happy.”

I thought about that. All advice is autobiography. Something bad had happened to Maddie in her transition from girl to woman. She was telling me to do what she thought would have been best for her. But I had no better map for how to lead Jennifer. I said, again, “All right.” 

Maddie kissed my cock, through my trousers. “And she’d love you to fuck her. and to teach her how to please you. Eventually you will. But in the meantime you should wait, and make her wait. Spank her, make her undress completely and bend over your desk naked for the cane: whatever you think she deserves. Then comfort her until she comes. But don’t take her yet. Let her make the move when she’s ready. She will.”

“Hmmm.” If Jennifer had come, there’d have been no stopping us. I’d have tipped her onto her back, on the floor of my office, and taken that virginity. That was why I’d had to stop so suddenly. On the other hand, Maddie’s approach seemed likely to introduce Jennifer to some of the wilder pleasures, while imposing frustration on me.

Maddie applied her tongue to where the tip of my cock was. “And then when you’ve shown her out the door you can take that nice hard cock of yours into the photocopier room. I’ll look after it.”

“Ah, I see. Motives. I’m sure you will.”

“May I suck your cock, sir?”