Wicked Wednesday: A bright and rising weal

Claire bent naked over my desk, holding on to the further edge of the desktop, legs wide apart. I’d tapped the cane against Claire’s bottom, and asked her if she was ready for her caning.

She shook her head. “God, I don’t know. Sir! But… I guess I have to be. Yes. Yes sir.”

“Hold on tight.” And I swung the cane medium hard, catching her across the middle of her buttocks. Claire’s head rose from the table, and she made a pained grunt. But she kept her bottom presented for me.

I added the second stroke, exactly as hard, just three centimetres lower. Her grunt of pain was no louder. 

Her ass waggled from side to side, but she settled, perfectly presented within five seconds. When it took her twenty seconds to be back in position after va stroke, she would get that stroke again. 

I resisted the urge to strike her harder. This was to be a cumulative thing. The third stroke, lower still, caused a short frenzy of stamping feet, and this time she moaned, high and musical. The muscles in her legs tautened as she struggled to keep her ass still. I nodded, but said nothing, raising the cane again.

The fourth stroke caused her first real grief, and a howl of pain and woe. Her feet left the carpet and kicked, and her ass dropped, her lower belly pressed against the desk.

I counted the seconds. Within seven seconds she was back in place, her bottom carrying four new raised welts, each a twin track of red with a paler line in the middle. I gave her the fifth stroke, and her vocal response was louder, and higher pitched. It took her twelve seconds to have her body back in the abjectly inviting position I’d instructed her to assume.

She must have sensed me raising the cane for the sixth stroke, because she gave one short groan before I delivered it.

When it landed, on the crease of her buttocks and thighs, she cried, “Fuuuuck! Oh! OH! Oh fuck!” Her legs lifted nearly level with the table and she rolled in pain, kicking.

Maddie pressed Claire’s shoulders down, and murmured something into her ear, I don’t know what, to comfort her and remind her to get back in position. Claire’s bottom, now marked with a new bright and rising weal, wouldn’t keep still. At last Claire presented her ass again, up and arched for me, and groaned, “Oh sir, oh sir, please, please, oh god.”

I tapped her left inner thigh with the cane. “That was your first six, Claire. We’ll take a short break now, but the best thing you can do is stay in position while you wait. We’ve got a long way to go together, you and I.”

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 and 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, 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 3

Now she was standing before me, wearing only her silver-and-black panties, I realized even more powerfully what her clothes had hidden: Claire really was a very  beautiful, very desirable voluptuous woman.

For reasons that were half guilt and, I realized, half desire, she thought that she needed to be caned. I was starting to think I needed, or at least wanted, her.  I  also wanted to give her a compliment, but it would break the mood.

The silence between us reminded her. I’d said six strokes, and she’d had three. She looked into my eyes, and put her hands out again.

I raised the strap and swung it down on her left hand. After the clap of leather on flesh she raised her head and called like a wolf: “Hooooo!” I watched her breasts shake. “Thank you, sir.” She held out her right hand.

I strapped her again, and she jumped, and swore and took her hand away. I raised my eyebrows, and Claire offered up her palm again. “Sorry, sir. I’m just not very brave. Not really.”

I had wanted to praise her for her bravery. But I said, ”No, you’re not. You’re getting that stroke again, plus a penalty stroke. Keep your hand out, Claire, without any more fuss, or you’ll get the same on the backs of your legs.”

Oddly, that was the right thing to say. Claire relaxed a little, and said, “Thank you, sir.”

I gave her the fourth stroke again, and this time she took it in silence, except for a small, nasal sound of pain before she thanked me. Then I swung the strap down on her right hand, making the fifth stroke harder than any of the strokes she’d had till then. Claire suppressed a cry, through gritted teeth, closed her eyes and pulled her pain faces again, but she held her palm steady, and after a while she was able to breathe, “Thank you, sir.”

“You’ve got two strokes to go, Claire. The sixth stroke and one penalty stroke. Then we’ll be done. You can rub your hands for a moment, if you like.”

“Thank you, sir. Ahhh.” She rubbed her palms together, turning them as if she were trying to wash the pain off. 

Maddie knocked once while Claire was still rubbing, and immediately entered. Claire grabbed for her breasts, covering them with her hands. I said, “Claire. Get your hands away. Put those hands at your sides: now!”

Claire swallowed and stood there, almost naked, waiting for my next instruction. She was blushing a little. I had to work hard not to smile. “Maddie?”

I’ve called the two shops. Yes, they’ve had stock shrinkage. If we can stop that, and return the clothes in good condition, they’ll be happy not to prosecute.”

Claire made a sound through her nose. She’d have thanked Maddie imperiously, a while ago, but now her punishment had started, she was in a very humbled state of mind. 

I said, “Thank you very much, Maddie. You’re a good … secretary. Now, Claire, we’re not quite finished dealing with you, are we? Hold your right hand out.”

Claire obeyed. The world was doing too many strange things. But obedience was safe. Maddie stared at her, openly. She said, “You really do have beautiful breasts, Mrs. O’Donnell.” I raised the strap. Maddie did not leave.  

Wicked Wednesday: The shoplifter’s mother and the strap 2

I raised the strap over my shoulder, and then swung it down, so it impacted on Claire’s proffered palm, with a loud crack.

“Jesus!” Claire gasped, and gripped her sore right hand in her left, then shook it.

“We’re going to have that stroke over, Claire.”

Her face fell.

“And this time, when I’ve strapped your hand, you hold it in place. Keep your palm upwards, and don’t take your hand away again. That’s a warning. Can you do that?”

“Yes, sir. I’m sorry sir.”

I raised the strap again. Claire suddenly said, “Thank you, sir. Even if I messed it up. Thank you, sir.”

“That’s better.” I swung the strap down again, landing firmly across that right palm. Claire shut her eyes tight and pulled faces, unhappy, painful faces, but she made no protest and her hand stayed held out for me, in place. She took three deep breaths and said, “Thank you, sir.”

“Good. Other hand. Hold it steady.”

Claire held her left arm straight out, her palm flat and uppermost. She gazed into my eyes. I swung the strap down, on her left hand. After the ringing impact she shook her head but managed to keep her palm out. “Oooh. Ow! Oh! Fuck! Thank you sir!”

I smiled at her. “Keep that left hand in place, girl. But you’re doing well, Claire. When were you last punished?”

“At school, sir. My husband … he thought of it as punishing me, but he wouldn’t do it like that. I like authority, like you’re giving me, but he didn’t understand how it works. He’d never be fair. Not careful like this. And certainly not when I wanted. He’d just hit me. With his fists.”

I shook my head. “Claire, we’ll talk about this.” She nodded. “Skirt now. Off!”

She’d already undone the clasp. Now she unzipped and stepped out of it. She wore pantyhose underneath, and below them panties, with a black and silver pattern. I said, “”Pantyhose, too.”

Claire smiled. I supposed she hadn’t stripped for a man since her husband’s friend. She tugged the hose down over her bottom and hips, and then slid them down her thighs, bunching them below her knees, and then pulling them off by the feet. She stood facing me in just her panties, her hands – no doubt very hot and sore – at her sides.