Wicked Wednesday: Cry if I want her to

Jennifer stood there in my office, little tartan skirt lifted at the back, panties down to her mid-thighs, waiting for Maddie to smack her with the ruler. She’d agreed she deserved this encounter with the ruler, and now there was only the agony of anticipation.

I said, “Good girl. You’re right; you do deserve it. Now, today’s going to be a little different from our earlier sessions, Jennifer. The first difference is that you’re going to count, today. You can treat this little ruler-spanking as a practice. After each smack, you’ll count it out loud, and then you’ll say thank you, to Maddie, and to me. Understood?”

Jennifer had her arms round my neck as I held her still. She looked into my eyes. Something in this situation was making her smile. “Yes, sir. I count, and I say thank you, to both of you.”

“Good girl. That’s a good girl who wants to learn.” Jennifer beamed, a very happy girl, about to be spanked. “Now, you make sure you count out loud as I’ve told you.”

“Oh yes, sir.”

“Maddie, not too hard, for these. Just make sure she feels them. Go.”

A second later there was the characteristic SNAP of wood on flesh, and Jennifer jolted in my arms. She pressed against my cock, and felt the involuntary movement I made in response: a pelvic thrust, for Jennifer. She held me tighter, and lowered her head to rest against my chest.

“Oh, sirrrr:” it was almost a purr. Then she remembered and said, “One! Thank you, Maddie! Thank you, sir!” A moment later, after a few seconds’ thought, she said, “May I have another?”

“Maddie, oblige the girl.” Maddie did, and the girl jolted again, in my arms, pressed against my fully erect cock.

“Two! Thank you, Maddie! Thank you, sir! May I have another?”

I had to laugh at Jennifer’s earnestness, in times of physical punishment. She was such a sweet girl. “A little harder, I think, Maddie.”

Maddie said, “I have to agree.” The third smack was possibly twice as loud, and this time Jennifer had to breath a few times, before she could count and thank. She had the sense not to ask for another.

I said, “Good girls. Both of you.” Jennifer, who was nobody’s fool, shot a look at Maddie. Maddie was a good girl too?

“All right, Jennifer. I told you today is going to be a little different. Take your clothes off, and hang them up, please.”

She glanced at Maddie, and looked at me. “Sir? Everything?” She hadn’t been naked in front of me before. 

“Do as you’re told, Jennifer. Maddie will help you, if you need it. But if you take too long about it, Maddie can show you that that ruler isn’t always a toy.”

She blushed. “Um.” She turned to face the wall, and took her blazer off. She unbuttoned her shirt, and took it off, revealing her bra strap, crossing a pale, slender back. She reached for the catch.

“No, Jennifer. Skirt next.”

“Yes, sir.” She unclasped and unbuttoned the skirt, and hung it up. Then she took her shoes and socks off, putting her socks inside the shoes and placing them neatly on the floor under the rack.

Then she turned to face me, in her bra and panties, arms still protecting her modesty. That, of course, would not last.

Jennifer was beautiful, with just a little puppy fat at the tops of her thighs, a very appealing dome to her tummy, and her breasts just a little fuller than I’d expected. She looked every inch a girl who was about to get the slipper. She was very aware of her situation: this was her party, and she’d cry if I wanted her to. 

 

 

Wicked Wednesday: Jennifer learns about Maddie

Note re Wicked Wednesday prompt: If I ran an erotic site, it would feature content a little like… this.

 

That afternoon Maddie had discussed what would happen when Jennifer arrived after school, for the second half of her slipper spanking. I told Maddie that when Jennifer arrived she was to bring the girl in, and remain in the room to provide assistance.

“Like, holding her down while you give her the slipper?”

“Yes. Also, I think it’s time she knew that she’s not the only girl who gets in trouble here. And maybe it’s time we made it clear that we’re not just headmaster and secretary.”

“So, I call you Master in front of her, and you threaten me with the slipper too? Or even give me me some while she’s there?”

“You won’t call me Master in her hearing. It’s too soon for that, I think. And I won’t punish you in front of her, unless you misbehave.”

Maddie smiled. I’d removed an important part of her privileged status. It was possible for her to be punished while Jennifer watched. 

“But I hope you’ll behave yourself, Maddie, so I don’t have to. But you might tell her you get the slipper or the cane too, when you misbehave. I think that’d help her, if she can feel that there’s someone else who knows what she’s going through. And that she can talk about things with you.” 

Things. Did you mean feelings? Master.” Her voice was so innocent.

“Careful, Maddie. But yes, Jennifer’s going through experiences she hasn’t had before, and of course she’ll be confused about her response to it. It’d be nice for her, I think, if she’s got someone to talk to, about her feelings.” 

“Does she get to find out that you fuck me, every time you’ve dealt with her, the moment she’s out the door?” 

I thought. Part of me resisted the idea. But Jennifer’s responses to her own submission were obviously and beautifully sexual. She should know that those rewards were there ahead of her, waiting. When the time was right. I nodded at last. “Yes, she can learn that.” 

“Wise Master.” Maddie kissed my nose, and caught a solid swipe with my hand on her bottom as she skipped out of the room. School would end in about twenty minutes. In about twenty-five minutes Jennifer would be in Maddie’s reception, waiting to be taken through to my office to be punished.

Jennifer was on time. Maddie opened the door and ushered her through into my room. Jennifer stepped inside, aware of Maddie following her. She smiled at me, wanly. She’d have rushed me and kissed me, if Maddie hadn’t been with her. But she wasn’t sure what she could do or say, in front of a third party.

“Hello, Jennifer.”

“Hello, sir.” She was almost sullen. She didn’t want Maddie here. I smiled at her, and beckoned with my finger. She came warily closer, and stood up straight, in front of me.

I laughed. “Oh, don’t be a silly girl. The slipper is your problem for today. Maddie really isn’t.” Jennifer didn’t look at all convinced of that. I smacked her bottom, and kissed her.

She lost her resistance in three stages: first, submitting to be kissed, then, a few seconds later, relaxing and enjoying being kissed, and after about twenty seconds she put her arms round me and kissed me back.   

At last I pushed her back a step. She looked happier and her mischief was back.

“How’s your bottom?” I asked.

“You’re going to see for yourself in a moment, sir!”

“Maddie, could you fetch a ruler from the cupboard, please?”

“Yes, Mr Beecham.” 

“Jennifer, I asked you a question. I meant, how does your bottom feel? Is it still sore?”

“Yes, it is, sir. And it is hard to sit down still. But… it’s not as bad as it was yesterday. Or as it’s going to be after this.”

I held her again, and she nuzzled, then kissed my neck. I said, “Thank you, Maddie. Could you lift Jennifer’s skirt at the back, please? Good, hold it there. And you can take her panties down to her knees, now.” Jennifer shook a little, as her panties slid down and her bottom was bared. She hadn’t been prepared for punishment by anyone but me.

I held Jennifer and looked at her while I spoke. “Now, Maddie, you’ll give Jennifer three smacks on her bottom with the ruler.”

Maddie smiled at me. She was always submissive with me, but I knew she sometimes enjoyed the other role.

She took the ruler from the desk, looked at Jennifer’s paled, shocked face for a moment, and smiled brightly at her. She stood behind Jennifer and drew her arm back. I said, “Just a moment, Maddie.”

I kissed Jennifer again. “Why are you about to get a tiny little spanking?”

“Because you asked me how my bottom was, and I was cheeky, sir.”

“So you deserve it, don’t you?” 

Jennifer frowned. She hadn’t expected or wanted to be spanked by someone else. But at least I was holding her. She looked down. “Yes, sir.”

Wicked Wednesday: The desk warmed by Jennifer’s body

Jennifer, released after the first half of her skippering, looked at her panties, and considered how they’d feel on her glowing red bottom. She’d asked me for permission not to put them back on.

I considered some options, including putting them on her myself, with smacks for any fuss she made. But she’d just come so beautifully, bent over my desk, and as far as I was concerned she could do no wrong, and she must come to no harm. So I said, “I suppose that’s all right, Jennifer. After this skippering, I don’t think you’ll be wanting to flash anyone, not for a few days at least.”

“Oh sir, never again. Believe me.”

She reached for her blazer and put in on, dropping the panties into the left pocket.

We looked at each other. Jennifer broke the moment, running at me and kissing me. I kissed her back, gravely, one hand in her hair. With my other hand I lifted her skirt at the back and rubbed her bottom, her skin hot under my hand. She kissed me again, softly, thoughtfully, while I stroked her. But after a few seconds I gently disengaged her. “You’re a good girl. But you’d best go home, now.”

I pushed the button on my desk phone, and said, “Maddie, make out a taxi chit for Jennifer, and call her a taxi to take her home, right now. And when you’ve done that, come in and bring me my notes on the swimming pool.”

I turned to Jennifer. “Girl, you will wait in Maddie’s office now, until the taxi arrives. Go to the taxi when it arrives. You’ll see it, through the window. Tell the driver to take you straight home, and give him the taxi chit when you leave. That’s it for now. I’ll see you back here after school tomorrow. Why is that?”

“Because you’re going to give me the rest of my skippering, sir.”

“That’s right, Jennifer.” I lifted her skirt again. “Eighteen strokes. So you’d best make sure you behave yourself all day, tomorrow, hadn’t you?”

“Oh, sir. I don’t want any more strokes. Eighteen will be…” She smiled at me. “Enough to be going on with. I’ll be soooo good, all day. Sir.”

“You respond well to discipline, Jennifer. You really do need it, don’t you?”

She touched her bottom, then quickly took her hands away, remembering that she wasn’t allowed to comfort herself. “Yes, sir, it seems I do. Thank you, sir.”

I held the door for her, and she stepped into Maddie’s domain.

In a few minutes Maddie arrived in my office. She had papers with her, though she was only carrying them as a show, for Jennifer’s sake. She dropped them on the chair, and, without a word dropped her skirt and undid her blouse, bending over the warm part of the desk where Jennifer had just lain. 

I condomed up and entered her, taking the higher, tighter orifice, since I couldn’t give her the slippering I felt she needed, or I needed to give her. Jennifer was not to know that Maddie was subject to discipline as well. Not yet.

Maddie took me in silence, aware of Jennifer just a wall away, until she grunted at one thrust that also lurched the desk forward. I reached under her and stroked her pussy. I wanted to take my time, but the sounds Maddie had heard from her office had made her as aroused as I was, and we lasted only a few minutes. We struggled to stay silent while we came.

Later, we heard the taxi honk and Jennifer sing out a “Bye, sir!” We went to the stock room. I pulled out the spare mattress, some blankets and pillows and we lay together fondly, Maddie and I.

Wicked Wednesday: Repair work for spanked Jennifers

Jennifer had just taken a dozen smacks with the slipper. It seems like a cosy, domestic implement, but in fact a firm slippering hurts much as the cane or paddle. She had another eighteen strokes to go, and I’d offered her a break, if she wanted to come back and finish her slippering tomorrow. 

It was always a dilemma. One the one hand she felt she couldn’t take any more. On the other, it’d mean she had more of the slipper to look forward to and twenty-four hours to think about it.

At last she said, “Oh sir, I wanted to take it all today. I was trying to be brave.”

“Of course you were brave, Jennifer.”

“But the slipper… it doesn’t care what I try to do. I don’t think I could stand more, sir. Not now. Can I come back tomorrow? For the rest? Please?”

I paused, as though it were a hard decision, though I’d offered her the choice just a few seconds earlier. At last I said, “Yes.”

“Thank you, sir.”

I said, “Can you stand?”

“I think so, sir.” Jennifer slid to her knees on the floor. Her hands hovered near her bottom, but she thought better of touching it. She put her hands on her head, instead. She wanted to be good, and for me to see that.

“Oh my god, sir. I’ll never. Ever. Do that again. Oh my god.”

I stood up, my cock still tenting my trousers. I felt sorry for her, but I also desired her. I imagined the heat of her bottom blaring into me, while she knelt on the carpet and I took her from behind. I held out my hand.

Jennifer saw my erection, but made no comment. She’d seldom known me not to be hard, when she was in my presence; it was a fact of life. She took my hand, and I helped her to rise, shakily, onto her feet. Then I held her.

“Here,” I said. “Just lean on me. You can cry, little one. And you were very brave. The slipper is a much fiercer implement than most people think. It’s ok not to be able to take two dozen in one go. You did well.”

“Thank you, sir.” She leaned in against me. She sniffled, once, but the tears did not resume. “I tried so hard. But it hurt so much. I don’t think I’ll sit down for a week.”

“You’ll be surprised how fast you recover, Jennifer. Which reminds me. I want you to bend over my desk now.”

“Oh sir! You said–“

“Silly girl. This isn’t punishment. This is repair work, for spanked Jennifers. Like yesterday. I’m going to put some lotion on your skin, to reduce the pain, and cool it down and reduce the swelling. So: are you going to bend over so I can cool you down, or do you want a touch of the cane first?”

“Sir!” Jennifer moved at light speed, it seemed. She was over my desk, legs apart in what seemed like no time at all.

I took the lotion from the cupboard. “I should say that this is rather… personal, Jennifer. When I apply the lotion I’m going to have to touch you in a very intimate way. As you recollect. You can have Maddie in to supervise, or I’m sure she’d be delighted to do it for you.” 

“No! Please sir, I’d rather it was you. Only you.” I knew, as she did, that with those words she was giving me a lot more than either of us were saying. Aloud.

“As you wish. Then turn your head, so your cheek rests on the table. Arms out, over your shoulders. Good.” I uncapped the lotion.

Wicked Wednesday: Janie’s drop #5

The previous episode is here.

Monica had said that Janie was better, when she was afraid. There was a pause. Then Janie said, “Yes, Mistress.”

“So. Here’s why you shouldn’t come, little Janie, unless I tell you to. Have you ever spent a night hanging from the ceiling by your ankle cuffs, getting a whipping every hour, on the hour?”

Janie thought about what that might be like. She had no doubt that Monica would do it. “No, Mistress, never.” Her voice was awed.

“I’m half tempted to give you the experience, then. You’d never disobey me or your Master again. Would you?”

Janie shook her head, eyes wide. “No, Mistress!”

“But if you come, Janie, that is what will happen to you. So control yourself, little slut.”

“Yes, Mistress.”

Monica fucked her for perhaps an hour, sometimes excruciatingly slow, while the little vibrator worked inside her, sometimes fast, pounding Janie’s bottom with her belly and thighs, the artificial cock bigger and longer than Paul’s. Janie had to fight the urge to release, sometimes gritting her teeth and crying with the fight to keep her orgasm at bay. 

At last she begged, nearly exhausted, “Please. Please, Mistress.” 

Monica withdrew. She rolled from the bed onto the floor. “You do not beg! Stay in place, Janie. Bottom arched up, just a little more.”

“Yes, Mistress.” Janie did her best to comply. The first stroke of the riding crop landed across her thighs, about two inches below the crease of her buttocks. It felt like pleasure, like the missing, vibrating cylinder. Janie huffed air through her nose. The next stroke landed an inch higher. Janie fought for control while Monica whipped her. She never been in danger of coming from the ministrations of the riding crop before.

Janie lost count of the strokes. Monica was panting lightly when she’d finished with her. Her body burned while Mistress warned her again about what would happen if she came, and allowed her, at last, into bed. Monica’s bed. It was after midnight, and Janie was exhausted.  

Before she slept she reflected that there was nothing terrible about how Monica tasted, or anything bad about the feel of her wet pussy in her face. It was ok. But it hadn’t done anything for her, sexually. So why was she so wet? Why did she need, so hard and so desperately, to come?

The next episode is here.

Wicked Wednesday: Janie’s Drop 4

The previous episode is here.

3

Janie spent Friday night, after her punishment, being taught to pleasure a woman. Monica kept the terrible leather paddle in her hand while Janie served her, and Janie felt it often.

There were so many things in cunnilingus that she could do wrong, she discovered. She had to discover, focus on and follow the rhythms of Monica’s desire, serving her, pleasuring her, responsive to her every change in timing or intensity.

When she was mistaken Monica used the paddle on her bottom, harshly and frequently.

She never showed Monica any lack of enthusiasm. That terrible session when she bent over the trestle while Monica paddled her: that was enough to make her forget any scruple, any distaste, any lack of pleasure in applying her tongue, her lips and nose to Monica’s cunt. Paul had sometimes punished her more painfully, but never so coldly. She was terrified of being so ruthlessly and painfully thrashed again.

In the meantime Monica lounged under her, sometimes holding Janie’s hair and pushing her head down, sometimes squeezing her face between her strong thighs. Sometimes Monica gasped with pleasure, and there was a respite from that agonising paddle.

But only for a few seconds, and never with a word of praise. 

Janie served her Mistress’s pleasure, every muscle in her body, and all of her concentration, directed at pleasing her Mistress and avoiding punishment. She would do nothing that incited Monica to punish her.  

At last Monica announced she was satisfied. (She’d come four times, Janie thought rebelliously: she bloody well ought to be satisfied. Then she turned white with terror, just for having that thought. Somehow, she feared that Mistress might know.)

Monica ordered her onto her bed, on her hands and knees, thighs widely spread, bottom arched up. Her Mistress put a blindfold round her eyes. She was aware of rustling sounds and then a click behind her.

And then a presence, cocklike, pressing at her cunt, and pushing forward. Monica was riding her, fucking her, with a strap-on. At first she wondered what could be in it for her Mistress, since she could receive no sensation from a silicon cylinder. 

But then there was a tiny sound, and the cylinder inside her began to buzz, slowly at first and then insistently. The cylinder began to drive into her, and nearly out again, and in. Her Mistress was fucking her, her hips swinging, the device in her cunt driving Janie higher and higher. Janie made a joyous sound: so much pleasure she wanted to sing.

Then there was a flash of pain: a riding crop striking hard on her left flank, then again on her right. 

“No, Janie, you haven’t earned an orgasm. I could feel you getting near, little slut. But you’re to control yourself. You’re here to serve, not to get off, little slavegirl. You may not come, is that clear?”

Her cunt clasped that strap-on. It still pushed her, relentlessly, to pleasure and release. Please, she wanted to say: oh, please, I want it so much. Please let me come. Please. But she said, “Yes, Mistress.”

“You have a lot to learn, Janie. Still, a little fear seems to improve you. At least you’re likely to be trying.”

The next episode is here.

Wicked Wednesday: Janie’s drop #3

The previous episode in this story in here.

Monica said, “Janie, I’m going to a party tomorrow. I’m bringing you.”

Janie blinked. “Uh?” 

“It’s a party you’re dressed for, just as you are.”

Janie nodded. To see how the words felt, she said, “Yes, Mistress.” They felt alien.

Monica didn’t react. “When I told you to to undress, Janie, did you obey immediately?”

Her heart sank. “No, Mistress.”

“Did your Master instruct you that you were to obey me as if I were he?”

She knew this woman was going to punish her. She so hoped this woman, her temporary Mistress, wouldn’t punish her. But it would do no good to beg.

“Yes, Mistress, he did. In the moment I forgot. I’m very sorry, Mistress.”

“Indeed. You knew better. I don’t want you embarrassing me with behaviour like that tomorrow. What would Paul do?”

Janie thought. She’d disobeyed, though only briefly. “Cane me, Mistress. Six strokes.”

“Appropriate. I’ll use the leather paddle. But ten strokes.”

Silence stretched on. Then Janie remembered: “Thank you, Mistress!” She sounded squeaky.

“Just in time, Janie. Bring the trestle to the middle of the room.”

“Yes, Mistress.” Janie hurried.

Then there were words, the beginning of a ritual. She’d never expected to hear a woman speak them to her “Bend over, Janie.”

Janie turned to face the trestle. She placed her feet apart, so they touched the trestle’s back legs, exposing herself to her punisher. There were grips, low on the legs on the other side. She lowered the upper half of her body, and held on tight. 

“I’m not going to call you a good girl for obeying me, Janie. That’s a given from you, the bare minimum.” The paddle cracked across her buttocks, and she cried out. Paul would have said something loving, to help her get through her punishment. And she always knew she’d be given an orgasm afterwards,  

But the paddle landed again. It was so hard and hot, nearly as bad as a hard stroke from Paul’s cane. Janie cried out again, abandoning herself to punishment, holding on tight. “You will learn to obey me, Janie.” 

On the third stroke, which landed low and hard, Janie began to sob. There were tears running from her eyes, down and into her eyebrows. “Without expecting praise or reward.” 

There was a pause. Janie knew Mistress would be watching the colour rise and deepen on her bottom. Enjoying it, like a connoisseur.

Janie wondered if she were a connoisseur of being punished. Paul was warm and loving, even when he hurt her. This was colder, and more impersonal. Still – she hated to admit it – there was something hot in that.

Then the paddle cracked down again, loud, and burning like fire. “If I have to teach you this lesson again, Janie, you’ll get ten with the cane as well.”

Monica stopped lecturing now and calmly, unhurriedly, completed Janie’s paddling. Janie sobbed throughout, lost in pain and humiliation. 

At last it was over, and Mistress commanded her to stand up. Janie struggled up, weeping, her bottom sore and, somehow, heavy. Monica held the paddle to her lips. Janie knew what she had to do. She sniffed, wishing she dared to wipe her eyes. She kissed it.

 

Wicked Wednesday: Janie’s drop Part 2

[I’m taking a break from the Maddie saga, because I’m flat out working. Here’s something I prepared earlier.]

 

Janie’s Drop #2

The previous episode is here

 

Monica was tall, dark-haired and slender, in a tight black dress. She’d kissed Paul at the door, ignoring Janie. They talked quietly. Janie looked around an ordinary room. Ordinary except for the trestle in the corner. She had to admit she knew what that was for.

Paul and Monica were watching her. Monica nodded. “Strip, dear. Completely. Kneel beside your Master.”

Janie looked at Paul, beseeching. He said, “I told you to obey her as you do me. You’re being insolent, Janie.”

Janie removed her shirt, then wriggled out of her skirt. She took off her sandals and knelt, body upright, hands by her knees. She stayed close to Paul. She was afraid of Monique.

Monica looked at her the way Paul did, as if she were the most fascinating thing in the universe. She didn’t think she liked it from Monica. She loved Paul. Anyway, she didn’t like women. Not sexually. Monica smiled at her, but addressed Paul. “She has lovely breasts, and a perfectly adorable little bottom. I’m sure you make her serve you often.”

Serve, thought Janie. She pleased Paul any way he ordered, but they made love. But Paul only said, “Yes. She’ll serve you too, of course.”

Oh god no, please, Janie thought. She could feel the heat in her face.

Monica walked behind her. “Oh! And she’s been punished!”

Janie wanted the floor to swallow her. She wore the trace of Paul’s cane. Twelve strokes, for not calling her mother. Three days ago:  the marks had barely faded.

Paul smiled. “You can discipline her, for your pleasure or as punishment. But tell me if you have to punish her.”

“Naturally.”

“Why’s that, Janie?” The sharpness in his voice helped her guess.

“So you can give me the same when you return. Master.”

 “Good girl. Clever girl.” She liked his praise. Janie relaxed a little.

Paul said, “The airport’s waiting. Janie, kiss my feet.”

Janie dropped to her elbows and knees and lowered her face, touching her lips and tongue to his shoe. Her cunt felt it hard, as always: it was something loving she did for him, and it made her feel utterly and deliciously submissive.

While she moved to his other shoe, Paul said, “I expect her back in good condition. Stripes and bruises, fine, but no damage.”

“Understood.”

Paul shook Monica’s hand. It was a transfer, thought Janie. He looked at her, hand on the door, and she knew that, harsh as he was trying to be, he’d miss her too. Then he was gone.

 

The next episode is here.

Wicked Wednesday: Lucy’s face

The previous episode is here

 

Sir, the cane in his hand, said, “All right Lucy. Now bend over the desk. Good girl.”

I watched Lucy, her eyes fixed on mine as she bent lower, her lovely breasts descending, and then flattening as her body touched the table. Now I could only see her back, and the upper slopes of her bottom.

“Put your hands under your Mistress’s thighs. Good. Hold her, and don’t let go or you’ll get extra. And where does your face go?”

“In Mistress’s pussy? Sir?”

“Clever girl. Bend a little tighter now, so you can reach.” Lucy wriggled forward. I felt her hair against my thighs, and then her nose and mouth.

Then she kissed my cunt. I sighed. The joy of it was so intense I nearly fell backwards.

“Now pleasure your Mistress, Lucy. Have you licked a girl before?” She couldn’t speak, and the head between my thighs turned, side to side, as if she was burrowing in: No, she hadn’t.

Sir caught my eye. He smiled. “Well, Lucy, this may be your first time. But I think you know what to do. Put your tongue out, and keep it busy. The cane will do the rest.”

Sir lined the cane against Lucy’s bottom, across the fleshiest part. I wished there was a mirror, so I could watch it land. But I’d know, of course, every time Lucy jolted. “Maddie, I expect you to keep Lucy behaving, and obedient. If she stops pleasuring you, even for a second, I want you to tell me. Is that understood?”

Lucy was already tonguing me. I had trouble speaking. “Yes. Hrrrm. Yes, Sir, I – Uh! – will.”

“Good girl. Mind you do.” He tapped the cane twice against Lucy’s bottom. “All right. we begin. Be a good, brave girl, Lucy, for me and your Mistress. We’ll make sure you come to no harm, little one.” I felt her nod. Every movement she made felt good.

Sir stepped to Lucy’s left. Poor Lucy sensed that, and she licked me harder. Our good girl.

Sir raised the cane over his shoulder. 

Wicked Wednesday: Maddie’s tale

The previous episode is here

Sir had said I was going to enjoy helping him to give Lucy her first caning. I felt a little guilty about that because Lucy was only going to get the cane because she’d been told to hold me down, and I’d deliberately got up, just to get her into trouble. I planned to start disciplining Lucy myself, soon, but I didn’t want to hurt her just now. So I said, “Sir?”  

“Maddie, I want you to sit on my desk.”

“Yes, Sir.” I rested my bottom on his desk and swung my legs. “No, not perch on my desk. I want you to get right up on top. And right over to the other side of the desk.” 

“Ok, sir.”

And I clambered up, aware of both Lucy and Sir watching me. So I sat in the middle, my knees up, arms over my knees, looking at them. 

“Good girl. Now skootch a little further back. So you’re on the far side of the desk. When my chair is.” 

I skootched. His desk was oak. The wood was so hard and cold, under my bottom and thighs. “Sir?” 

“Good girl. Now spread your knees, wide apart as you can. Good. What do you think, Lucy?”

Lucy stood beside Sir. Her thighs were trembling. She said, “She – Mistress. She looks very hot, Sir.”

Sir put his arms round Lucy and turned hewr to face him. He cuddled her, and whispered, “Don’t be afraid, Lucy. The cane hurts, but you’ve known it was going to be part of your life since this morning, haven’t you?”

“Y-yes, Sir. I have. But I’m still afraid.” She leaned in against him, put her arms round him. I knew how lovely and luscious Lucy felt. I wished it was me, in her arms. 

“Lucy, what you’re afraid of, lovely little one, is mostly the unknown. All the terrors of your imagination. You’ll find this is going to sting, and it’ll mark for you a few days. But it’s not as terrifying as you think. You’ve got Maddie to thank, for you being just about to get your first caning. You know that, don’t you.”

“Sir! I let her get up when you told me to hold her down. I failed, Sir.”

Sir smiled and smacked Lucy’s bottom lightly, then let his hand stay there, squeezing. Lucy wriggled.

“Yes, but she got up, Lucy, darling. She wanted you to get the cane today. She was turned on and she wanted to watch you be punished too. But she also did you a good turn. It’s better to get the cane early, than to fear it and let the fear build up until it becomes something terrible. So I want you to turn now, and thank your Mistress for getting you caned.”

“Sir!?” Lucy sounded shocked. Then she thought, and nodded. She looked at me. Her tongue came out and wet her lips. I felt it in my cunt, when she did that.

Lucy swallowed, then spoke firmly. “Maddie. Mistress, thank you for making sure I got the cane today. It is better if I don’t have to wait. So thank you.”

Sir smacked Lucy’s bottom again. A little harder, leaving a pink print this time. But he said, “That’s good, Lucy. Well done.”

Lucy smiled and cuddled in again, her breasts heavy and so pale, crushed against his jacket. Sir kissed her forehead, then looked at me. “Good girl, Maddie. Now lean back. Put your hands on the edge of the desk, behind you. And push your pussy forward a little. No, more. That’s good. Don’t move out of that position until I say.”

He stepped back from Lucy, then picked up the cane again. She was being brave, but now her caning was about to happen I could see tears glistening in her eyes. He whispered something to her. I couldn’t catch it but it was loving, encouraging.

He held the cane under her chin, to lift her head. Then he touched it to her mouth, and she kissed it. Slowly, almost reverently.