Wicked Wednesday: That fierce grip

I’d told Claire to arch her ass up, as though she was begging for the cane.

“Yes sir!” Claire’s bottom rose off the desk, round, sweetly curved and decorated with five glowing bands from the ruler in Maddie’s hands. Bent over, her legs straight and widely parted, ass poised, she was in one of the most sexually abject an inviting positions a woman can assume.

But I gave her no praise, instead tapping her bottom with the cane, not softly. I growled, “Keep your ass right there, girl. You’ve go twenty seconds after each stroke to get back in this position. Or you’ll get extra strokes.”

“Yes… S-sir.” Claire was having trouble speaking.

I wondered whether to make her count and thank me for each stroke, but I guessed that she’d lose what remained of her ability to speak in the first four strokes. Maddie could do the counting.

That raised another question: how many strokes to give her? On the one hand, I considered she’d done nothing wrong; but she felt intense guilt, and her caning had to be impressive enough to end that guilt. Not less than two dozen, I decided, and possibly three dozen. More if she wasn’t sobbing.



“You’re in charge of looking after Claire while I cane her. Comfort her, give her tissues, say nice things. Look after her. Sister to sister.”  

Maddie crossed to Claire’s side. She bent forward and kissed Claire’s bare shoulder, then her neck. And she put her hand on one of Claire’s hands, which were fiercely gripping the edge of my desk.

Maddie whispered, “It’s going to hurt, little darling. But you’ll get through it. I’ve been in your place, on this very desk, and I can promise you you’ll be all right. There.” 

I tapped the cane on Claire’s bottom again. “Ready, Claire?” It was a ridiculous question, but a traditional one.

Wicked Wednesday: Moving fast when motivated

I used the strict-Headmaster voice. “Right, Claire. You’ve asked for the cane, and now you’re going to get it. Good and hard, girl.”

Claire looked solemn. It was apparently the first time she’d been in this ritual since she left school. But she remembered its power. “Yes, sir.”

“Bend over my desk, Claire. Hold onto the far edge of the desk. And don’t let go or get up, if you value your skin.”

Claire scrambled to obey, presenting herself over my desk, breasts flattening onto the leather patch. She reached forward until she could get her fingers holding the far edge.

The position kept her body tautly stretched.

“Good girl. Now put your feet right apart. You don’t need modesty, from a man who’s going to fuck you shortly. And it gives the cane full access to your body. Deeply.”

I meant that when I caned her lower buttocks, the cane would get very close to her pussy lips, possibly reach them. Claire nodded solemnly. She knew what I’d meant. She let her face fall to the desktop, and spread her legs for me, very slowly.  

I said, “Maddie.”

“Yes sir?”

“Two ruler strokes for Claire, please. Medium hard.”

Maddie brightened. Her good luck wasn’t necessarily going to be appreciated by Claire, but it was luck, for both of them.

Maddie can move fast when motivated, and in less than three seconds there was the sharp slap of wood on flesh, then another, while Claire gasped. A fourth and fifth band of pinkish red bloomed across Claire’s bottom.

“Claire, when I give you an order, you acknowledge it by saying ‘Yes, sir.’ Understood?”

“Yes, sir. I knew that, sir. I’m sorry.”

“Good. And you obey orders quickly. Immediately. That may have stung a bit, Claire, but it was only a warning. The next time you fail to acknowledge an order, or to jump to obey it, I’ll make the point with the cane.”

“Yes, sir! I am sorry, sir.”

“That’s better. Now arch your bottom right up. Like you’re a cat begging to be fucked. But in this case, like you’re begging for the cane. Which in fact you are.”



Wicked Wednesday: Last chance to back out

“Maddie,” I said, as though I was displeased with her, and she became subdued.

“Yes, Master?”

“Fetch the cane. Not the senior cane. The medium. And at the moment, it’s for Claire and not you. Though that can change.”

“Yes, sir.” And Maddie turned away.

“Come here, Claire.”

“Sir?” She stood in front of me, her face – like her ass – still a little pink from Maddie’s semi-comic but eventually effective attempt at discipline. All of us had found it powerfully erotic, though, including Claire.

“Hands on head, Claire.” When she obeyed I raised my hands to her breasts, lifting lightly, simply for my pleasure, and perhaps hers. “I’m going to take these clamps off before I cane you. It’ll hurt a bit when the blood returns to your nipples, but it won’t hurt you too much. Maddie knows better than to put them on tight.”

Claire nodded, face scarlet, while I carefully disengaged the clamps. I dropped them in my pocket, and put my arms round her. She held up her face to be kissed, and my mouth touched softly against hers. Then we opened our mouths at the same instant, and the kiss became passionate. 

I put my hands on her ass and smacked her, not gently, and did what I could to distract her from the ache in her nipples. Eventually I drew back and looked at her. “Better? Are you ok?”

Claire put her hands to her breasts, and rubbed briefly. Then she nodded. “Yes, sir. My nipples are still, well, a bit hurty. But I feel very looked after.”

I dipped my head and held her breasts in my hands again, and kissed each erect and rubbery nipple, softly and reverently, in turn. Claire moaned. “Oh, that’s good. Thank you, sir.”  

“You know that I’m going to cane you very hard, don’t you? You’ll scream. Your ass will look like a tomato, and you won’t be able to sit down for days. You understand?”

“Yes, sir. Of course.”

“This is your last chance to back out. You can retreat now. But if you choose to continue, you won’t be allowed any more decisions. Not for a long time. So: retreat?” 

“No, sir. I’ve asked for this. I want it. I definitely need it.”

I looked into her eyes. I said, “When we’re finished here, I’m going to take you home and fuck you till we’re both exhausted. Then we’re going to rest and eat and I’m going to fuck you some more.”

Claire smiled. “Yes please. Um, sir.”

Maddie waited politely beside us, with the cane held out for me. I took it from her, and swished it the air, once, twice. Claire stared at me, and swallowed. Her real punishment was about to begin. She looked suddenly nervous.

But it was important that her mood, and the atmosphere, changed now. Claire’s caning had to be memorable, and hard enough for her to consider she’d been properly punished and could forgive herself. I held the cane below her mouth, so she had to lower her head to kiss it.  


Wicked Wednesday: “Grab your ankles, Claire”

Maddie had just told Claire that she was bending over because we wanted to watch her breasts sway while Maddie spanked her. So I said, “This is true.”

Claire glanced at me, pleased. One kind of tension had broken, to be replaced with a softer, erotic one. In that tension she was being punished, not by me, but by the woman who called me Master. She hadn’t expected that. It was humiliating, and it was hot. These things were complicated. 

Maddie touched Claire’s mouth lightly with the ruler. “Grab your ankles, Claire.”

“Do I say, ‘Yes, miss’?” Claire adjusted her position. Feet slightly further apart, the muscles in her legs tightening as she reached for and held her ankles.

“No, Claire. Maddie’s head is quite big enough as it is.” Maddie poked her tongue out at me.

I ignored it for the moment. “Just call her Maddie, even when she punishes you.”

Maddie raised the ruler again, and swung it down on poor Claire’s bottom. It was a much lustier, noisier smack than the first. The mark bloomed almost immediately on Claire’s soft skin, a bright red while the first line across her bottom was pink. Claire said, “Oow!” and stumbled forward. Then she remembered herself, stepped back and bent over tightly, hands back holding her ankles.  

The invitation was too much for Maddie, who raised the ruler again. The third stroke was, of course, harder still, and made Claire toss her head while she fought to stay down and in position. She gasped.  About a third of Claire’s bottom was now a very pretty pinkish red.

Maddie said, “That’s so lovely, Claire. You colour so very beautifully. Master’s going to love caning you.”

She raised the ruler again.

“That’ll do, Maddie. You’ll have to wait till she cheeks you again, if you want to give her more.”

Maddie put her hand on Claire’s bottom, and ran her fingers over the three marks she’d left. Then she squeezed lightly. “You’re very beautiful, Claire. And your body is just … yummy. It’s a crime that you haven’t been fucked in a year. Absolute madness.”

I could see that Claire was a little embarrassed, or perhaps flustered, by Maddie’s enthusiasm. I said, “You can straighten up now, Claire. You’re a good girl. But no more cheeking the staff.” Maddie, behind Claire, poked her tongue out again. 

Wicked Wednesday: Maddie, Claire and a ruler

Claire had said she wanted to be fucked after her caning. I said, “Oh, I can guarantee that, sexy woman. Though the caning comes first.”

She nodded. “I’m a little scared. But I deserve it. I need it. I want to pay.”

“Claire. Just one thing. The cane hurts, but it’s also meant to take away pain. When I’ve caned someone, whether a student or a … woman who needs discipline–”

Claire smiled. “Like Maddie here. I bet she gets really bratty, if you leave too long a gap between her canings.”

“Maddie, fetch the ruler.”

“Yes, Master.” Claire glanced at her sharply. She’d heard the change in my title. Maddie gave Claire a kiss on the cheek, and turned away.

I kept my eyes on Claire. “The thing is, you get the cane to get forgiveness. It clears your record. You start again, with a line drawn under whatever it was you got caned for, and you behave better in future. But you know that you’re forgiven.”

“Yes… Sir.”

“More to the point, Claire, it’s one of the rules that you have to forgive yourself. Once you’ve been punished it’s dealt with. You’re not to go over and over it in your mind, and feeling guilty. It’s done. Done hard, and then over with. You move on with your life. Is that understood?”

“Yes, it is. But please do it hard, sir. I know I can forgive myself. But I need to hurt first.”

Maddie returned, the ruler resting on her outstretched hands. “The ruler, Master.”

“No, Maddie. It’s for you to use. Any time you feel Claire’s being cheeky to you, you have my permission to give her a good whack. Or three.”

Maddie touched the ruler to Claire’s pussy. “Thank you, sir.”

Claire stared at me. “I didn’t give you permission to let her…”

“And I didn’t ask for it. Maddie? Continue, please.”

Maddie smiled at Claire. “Just bend forward a bit, Claire, and put your hands on your knees.”

Claire frowned, and then obeyed, the chain between her clamps swinging merrily. It should have little bells on it, I thought irrelevantly.

Maddie placed the ruler across the crown of Claire’s bare bottom, delightful though a little plumper than her own. Claire closed her eyes and waited. Maddie raised the ruler and swung it in, sharply. Claire grunted as it landed, but it was plain it hadn’t hurt much.

Maddie said, “By the way, I’m nearly the same as you. Number of days since I was last caned: one. Don’t be afraid, Claire. It hurts when it’s happening, but it never lasts long. And some people quite like the heat, and, um, other sensations afterwards.”

“Thank you, Maddie. I believe it. May I get up now?”

“No. I think we’ll have you bending a little tighter for the next one. Also, I said you have really beautiful breasts, and I think both of us, I mean Master and I, want to watch them sway.”



Wicked Wednesday: Resetting the calendar

Now we were fucking, cock to mouth, and I could feel tension and pleasure surging in me, wanting to overflow. I said, “Do you have an objection to swallowing?”

She took a second to understand the question, and she looked at me as if I was mad. Why would she object to swallowing? Why would it be up to her anyway? It seemed I was being too careful.

So I pulled her hair harder and held her face tight against me.

I came at last. She made an odd sound, something like “Lloorb”, when I flooded her mouth with salty fluid, and she swallowed, taking every drop into herself.

I slowed, breathing hard, and Claire continued to lick and suck, while I pumped her mouth, savoring those last moments of pleasure. She continued to work me, staring up into my eyes. I smiled down at her. “Good girl, Claire. You did very well. Thank you.” Then I withdrew from her mouth. “Put my cock back in my underpants, and zip me up, Claire.”

She was surprised. Most men in her life, so far, had done that for themselves. She’d experienced brutality, I felt, and abandonment, but never servitude. Servitude was, it seemed to me, something she was wired to enjoy very much. She said, “Yes, sir”, because she’d heard Maddie say that when given an order, and obeyed.

I grinned down at her and held out my hand, helping her up as if from an unusually deep curtsy. Her breasts, and the chain between the nipple clamps, bobbed appealingly. When she was standing I put my arms round her. I beckoned to Maddie, and she came and joined the hug.

We swayed together, the three of us. I sensed that Claire was happy, and her attention was somewhere inside herself at that moment. I looked at her until she returned and smiled back at me. “When did you last suck a cock, Claire?”

She smiled a little sadly. “My husband’s friend. About a year ago.” Then she smiled without sadness.

“Then we’ve re-set the calendar: Days since Claire sucked cock: O.”

She laughed a little. “Days since I’ve been fucked; I hope that re-sets too.”

Wicked Wednesday: The shoplifter’s mother clamped

Maddie knelt and applied the clamp to Claire’s left nipple, then put the other clip to her right.

A fine gold chain connected the two. Maddie tugged lightly on the chain, causing Claire to open her mouth further and let me push deeper. Claire made a noise around my cock. It can’t be transcribed, but it meant pleasure.

Something dark and powerful was stirring deep within her. Her lips closed on the base of my cock. I let her hear my pleasure.

Maddie stepped back. “Anything else, sir?”

I said, “Yes, Maddie, bring me the strap. Claire, if you let my cock slip out of my mouth before I come, I’m going to wallop your ass till my arm is tired. Understood?” She said nothing, but her head bobbed: assent.

I took the strap from Maddie, and let it trail down Claire’s back, as a warning and incentive.

“May I watch, sir?”

“Claire, do you mind if Maddie watches you suck my cock?”

Claire made another vocal noise, partly muffled by my cock, but I don’t think it had words in it anyway. It wasn’t indignation. It was sex. The idea of being watched pleased her very much.

I raised the strap and brought it down, not fast, so that the end of the strap wrapped under her right buttock and slapped her smartly but not too painfully.

Claire closed her eyes and sucked harder. I swung the strap again, a little faster, so its smack on the underside of her left buttock was harder. Her eyes shut tighter.

I could see pain in her face. “Keep your eyes open, Claire. Look up into mine.”

Guido Reni’s Magdalene practicing her fellatio face

She obeyed, her eyes helpless, pleading, pious, like a saint in a Guido Reni painting. I smiled down at her. “Good girl, Claire. You’re a little rusty, I know, but you get top marks for enthusiasm.” She made an acknowledging noise, in her throat.

I began to pump her, thrusting slowly into her mouth, taking it slowly so she could adjust to my rhythm. She choked once, as I thrust deeper, but a woman who asks you to cane her presumably won’t mind that.

I put my free hand in her hair, and pulled lightly. Not to hurt, just to let her know I was taking control. I thrust harder and faster, and she gamely followed me, keeping my pace.

Wicked Wednesday: Clamping down

Claire shook her head, panicked, mouth still full of hard male essence. I said, “Maddie has heard you get the strap. She knows you’re going to get the cane soon. She’s knows that afterward I’m going to fuck you with all my heart and soul, not to mention my cock. So is it a problem if Maddie knows you suck my cock?”

Claire was still, digesting this. After a few moments her head moved again, from side to side, my cock still firmly in place. No, it didn’t matter. I put my hand on her head. “Continue, Claire. Or I’ll strap your hands some more. You can get the strap while you suck cock, you know.”

There was a pause, probably as long as three seconds, though it felt longer. Then Claire took me deeper in her mouth, sucking hard. Her blush had spread to her breasts and shoulders. She’d accepted that sometimes she sucked cock in front of an audience. Maddie said, “Sir?”

“Nipple clamps. Fetch. Claire needs them.”

The nipple clamps were Maddie’s. They weren’t for use on schoolgirls. Or boys, I supposed. She went, leaving the door open, and fetched them from her drawer. “Sir.”

“Don’t stop sucking, Claire, if you know what’s good for you. And Maddie, Both Claire and I have our hands full just now. You can put the clamps on Claire’s nipples.”

There was a small dissenting sound, and a shake of her head from Claire. I put my hand on the back of her head.

“Claire, you know you can stop this at any time. But if you don’t want to stop, then you’re going to be wearing little clips on your nipples until I’ve come in your mouth. I noticed your reaction when I squeezed your nipples before.”

Claire said, “Ummmm, bbdddd…” A little line of drool escaped from the left side of her mouth. Then she moved forward, taking the whole of my cock into her mouth and throat.


Wicked Wednesday: The shoplifter’s mother, and the wicked games

Claire stepped quite naked into my arms. I reached down and patted and smacked her bottom, holding her tight. We kissed. Eventually, I said, “When were you last fucked, Claire?”

Claire looked at the floor. “That guy. My husband’s friend. A year ago. He stopped fucking me after Bill found out.” So I learned her husband’s name was Bill. I smacked her again, then reached lower, to part the cheeks of her bottom and touch her pussy. Of course she was a wet woman. She hissed again, that in-drawn breath, when my fingers found her, pressed her labia and pushed easily, wetly inside.

“I’m going to fuck you after I’ve caned you. You know that, don’t you, little Claire?”

She grinned. “I didn’t know it for certain.” It was happy knowledge. “But yes, sir, you may fuck me. If you cane me hard.”

“Hah. I don’t think either of those things is up to you any more.” Of course they were up to her. But we’d both have more fun if I said otherwise. She nodded gravely, as if what I’d said was true. I kissed her again, and raised my hands to hold her breasts, each a little larger than I could hold completely in one hand. I squeezed her nipples between my thumb and forefinger. 

She sighed. “Yes. It has been too long. I’m being greedy, I think. I want everything you can give me.”

“Good. Drop to your knees, girl.”

“You want me to suck your cock?”


Claire dropped to her knees, as instructed. She unzipped me, and fished out my cock, utterly hard and straight for her.

She looked at it for a moment, and said, “Mine. Well, it is for the moment.” She kissed the tip. I pressed the buzzer on my desk.

Claire had my cock deep in her throat, sucking intently, when Maddie said, “You called, sir?”


Wicked Wednesday: The shoplifter’s mother and the strap 4

I said, “Maddie’s quite right. You do have beautiful breasts.”

And I raised the strap while Claire watched me like a mouse watches a snake, and brought it down on her right palm. She hissed in a breath, and then stood there, feet slightly apart, not reacting. As though it hadn’t hurt, which it clearly had. I admired her self-discipline. She said, “Thank you, sir.”

“Good girl. Brave girl. Hold your left hand out now, Claire. The penalty stroke will be the last one, so long as you behave.”

Claire offered her palm. Her breasts trembled and there was a muscle all a-tremor in her belly, and her slightly plump thighs shook. Fear, I guessed, and excitement. She would need my cock – anyone’s cock, in a sense, but mine at this moment – seconds after I’d finished her caning.

I looked her in her eyes, and she stared back at me. She knew what she was asking from me, the unspoken things, and she knew she was going to get them. She had had a long sexual drought, and it was bout to break. Eventually, though the moment between us was very deep, and utterly serious, I smiled, and she did too, with relief.

I swung the strap down, hard, and it smacked on her hand, which she kept in place. This time she made the pain faces, hissing in her breath, without closing her eyes. She gazed at me while the pain sank in, and eventually said, “Thank you, sir.”

I said, as courteously and ceremonially as I could, “Thank you, Claire. Your strapping is over.”


“Thank you, sir.”

“From now on, Claire, you listen carefully to the orders I give you, and you obey them. Obey them quickly. But we’re done with that now. You can put your hands at your sides.”

“Sir. Thank you sir.” Claire relaxed, putting her weight on her right leg and bending the other slightly, like a Greek sculpture.

“Take your panties off, Claire.”

“Yes, sir.” She reached her poor strapped hands down, to tuck her thumbs under the hems of her panties, and shucked them swiftly down to her knees. She put her feet closer together so the panties fell to the floor, and then bent forward, breasts swinging, to pick them up. They joined the rest of her clothes on the chair.

I put the strap on the desk, so she knew it wasn’t necessarily gone. She could still feel it again if she disobeyed. But I said, “Good girl. Oh, and Maddie, that will be all.”

Maddie nodded, whispered a “Thank you, sir” at me, and left.

Claire waited, beautiful, naked, knees trembling slightly, about to be caned. She’d begged for the cane, but now it was coming it was still fearsome.

I held my arms out to her. “Come here.”