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: All slippery, and floaty

I poured a generous amount of the lotion onto her heated bottom. It took a lot, her skin seemingly almost drinking it in. But eventually there was enough for a creamy covering over the surface of her bottom, and I began to gently rub and stroke her, finger-tips at first, then increasing the pressure until I could feel her muscles. Jennifer had whimpered a little at the soft touching, but paradoxically made comforted pleasure sounds as the massage got harder and deeper.

Every movement I made tormented my cock, which ached for her. I need only unzip and she would welcome me into her and one, at least, of her virginities would have flown. But though I’m sure she longed for that as much as I did, it was still not the time.

But it was time to give her some relief. My massage had taken my fingertips into the cleft of her buttocks, to be received with soft sighs and murmurs. My fingers pressed on either side of her pussy lips, so very close but not quite touching. I whispered, “I think you could do with some massage here. Don’t you?”

“Oh, please. Sir…” Her voice was far away, as if she was dreaming.

“But you’re going to have to ask me, Jennifer. This has to be your choice.”

“I choose you to… No, I mean, please massage my pussy, sir? Please?”

I counted five seconds, then began to stroke her soft, plump, wet folds. Jennifer moaned, then, a second later wailed as if I’d spanked her again. Her appreciation was loud as I slipped one, then two fingers into her, and pressed the other two fingers against her clitoris.

We moved together, her slippery centre moving rhythmically forwards and back, up and down.

In less than a minute her hands and buttocks clenched, and she made a long, low, melodious moan like a whale calling in the deep to another whale, of surpassing and hypnotic beauty. Her mouth had opened wide, as had her eyes, and she flopped on the desk as she came.

I kept going, fingers working inside and outside her pussy, and she was soon wailing that cry again, body tense, her upper body clear of the table. As she came this second time I smacked her bottom hard, twice, knowing she wouldn’t feel it as pain. The sound intensified, and then with a grunt she collapsed again.  

A long time passed. I slowly withdrew my fingers, and leaned down to blow on and then kiss her poor tortured bottom. Eventually Jennifer opened her eyes. She looked at me as if she was surprised to know who I was. Or where she was. “Oh, that was so lovely.”

I smiled at her. “You’re so lovely, Jennifer.

“I feel so strange. Kind of floaty. Just… weird.”

“Yes. I’ll get Maddie to call you a taxi. I don’t think you should walk home.”

She looked at her clothes. “Can I dress now, sir?”

“Yes.”

Jennifer took her skirt, first, slung it round herself and did up the catches and buttons. Then she looked at the tiny panties. Her bottom was swollen, and for all that she was in a beautiful daze just then, it hurt. “Is it all right if I don’t wear these, sir? I’ll be very careful.”

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: Writhing, kicking and bawling

Jennifer heard me sigh. She knew I was appreciating the view she was giving me, over my lap. And she remembered why she was in that place. She said, “Please sir, please give me the slipper. Hard. Don’t show me any mercy, even if it blisters my bottom.”

Her voice was shaky, high-pitched, on ‘blisters my bottom’. She found that was a scary thought.

In reality I wasn’t going to raise any blisters, not on a first slippering. But a little fear would do her no harm. I said, “Good girl. You asked very nicely. And of course I shall.”

I placed the slipper on the crown of her left buttock, so she knew where the next wave of pain would arrive.

Then I raised it, drawing it up over my shoulder. Jennifer said, “Oooh,” when the slipper was gone. I let her wait while I counted, slowly, to five. Then I swept the slipper down, landing on her bottom with a solid, rubber on skin impact. The sound was louder than a pistol shot. Jennifer screamed, and her body stiffened.

I watched her fight for control, and brought the slipper down again. Both cheeks were showing a slipper-shaped mark, blossoming to a deeper red than the marks left by my hand.

Jennifer writhed and screamed and cried, her arms and legs flailing, while I held her in place and continued.

After the first six I concentrated on the softer skin of her lower bottom, and the volume and urgency of her cries escalated. I gave her the eleventh and twelfth strokes on the backs of her thighs, sending her frantic. She was weeping copiously, and the tears flew in the air as she wildly bobbed and shook her head.

I stopped after the twelfth stroke. “You’re halfway done, Jennifer, girl.” If she heard me she gave no sign, still writhing, kicking and bawling. I said, “Settle down, Jennifer. I’m allowing you this time to recover yourself. But you will be quiet and behave yourself.” Still no difference.

I let my voice become harder. “You lie still and keep quiet right now, Jennifer, or I’ll give you extra!”

That worked magic. She put her legs together and pressed her thighs down, over mine. She pressed her fingers on the carpet and pushed herself back a little, so her bottom was again in perfect position for me.

And she stopped her wailing, though the tears still flowed.

“Good girl,” I said. “Now, you have another dozen with the slipper to go. Plus six penalty strokes. Would you rather have them now, or come back to my office tomorrow to take them then?”

Jennifer froze. For a long time she said nothing. 

Wicked Wednesday: Kiss the slipper

I watched while Jennifer crawled to the cupboard, and opened it. It was a cornucopia, for her, of instruments and devices meant to restrain her, to constrict her and to cause her pain. They told her about her future. Her eyes were wide open. She made no sound.

Her mouth was open too, but she was fascinated rather than frightened. She was a girl who’d admitted she needed discipline and direction, and these items were for just that. She found the slipper and reached for it. She held it in her hand, and looked at me; crawling on hands and knees back to me would be awkward.

I said, as if I was annoyed with her, “Hold it in your mouth, girl! And come here!”

I sat back in the chair where she’d had the first half of her spanking. Jennifer crawled towards me. Her eyes were blank; she was focussed within herself. I think she was lost in this new reality, where strange, painful but sexual things happened, and she could neither predict nor choose what they would be. That was terrible, and it was hot.

I took the slipper from her mouth and caressed her hair with my hand, as though she were a cat, or dog. I said, “Still on your knees, but upright girl. Up!”

Jennifer straightened her back. I brushed hair away from her face with my fingers. “How are you doing? I know your bottom hurts. It’s meant to, I’m afraid, and you deserve it. But are you all right? Emotionally?”

“Sir, that was terrible. Awful.” But her eyes were clear, and she didn’t seem to feel that ‘awful’ was such a bad thing. “I know I deserved it, sir. And I want to clean the slate. I was behaving… very badly. But it huuurt. It still hurts. And I’m afraid of what comes next. The slipper’s going to hurt even more, isn’t it?”

“Yes. It stings like fire, I’m afraid, Jennifer. It can raise blisters on your bottom. Literally. But you don’t get as many strokes.  I think two dozen will finish this. Perhaps more, if you don’t keep still for me.”

“I’ll try, sir. But it’s so hard not to try to get away. You spank very hard, sir. If the slipper’s worse than your hand, I may go out of my mind.”

I reached down to the kneeling girl, and drew her in for a hug. “You’re going to learn, little one, that a sore bottom motivates good behaviour and deters you from bad. No matter how much it hurts, it happens because I care about you, and your well-being.”

She looked down, her hair falling over her face. I brushed it away. “I know you care about me, sir. I can feel that even when it hurts so much I think I can’t bear it.”

“Well, this won’t be the last time I make your bottom sore. And you’ll learn something else, which is that getting a sore bottom, when you deserve one, isn’t the end of the world. Girls have been getting spankings for thousands of years, and yet there are still girls.”

She frowned at that, and her brow cleared when she realised I knew I was talking nonsense. She smiled, and wriggled forwards in my arms to kiss my neck.  “Well, I’m only one girl. Am I going to get thousands of spankings in one year?”

“Well, thousands means plural. Two thousand spankings would mean I have to spank you six times a day, every day.”

“That’s silly, sir!”

“Oh? Silly?” My voice suggested that she might be on dangerous ground.

“Of course. You’d only have to spank me five point four-seven times a day. Five and a half spankings, with rounding up.”

I laughed, and then she joined in, giggling at her own silliness. “All right, Jennifer. It’s time, girl. Kiss the slipper.” I held it to her lips. She kissed the rubber side warily. “Good girl. Now get over my lap, bottom up, head down, and ask me nicely to slipper you hard. Without mercy, even if your bottom blisters.”

The corners of her mouth fell. She remembered where she was, and that she would be crying again, like a baby, all too soon. But she placed herself lithely over my knee. This time she held my shin with both hands to steady herself, and her thighs were a little open, all primness forgotten. Her little pussy pouted at me, damp and plump from her own arousal, in that softest valley between her buttocks and her thighs. I sighed at the beauty of it, and of Jennifer.

Wicked Wednesday: Jennifer in my office

The next day Jennifer came to my office as I’d told her to do, after school. She was wearing her new uniform. It was less cheerfully obscene than the too-small version her mother had bought, but she looked radiantly happy in it.

She looked at me, proud. Then she faltered, worried that I might think she’d chosen wrong. I said, “That’s perfect, Jennifer. It fits you perfectly. It looks, really, very good on you. Flattering. You did very well.”

She beamed. She wanted to feel confident. A girl who has felt a man’s cock harden for her has no doubt of her enchantment over him. But she still wanted to know she’d done right.

I pointed my finger at her, and made a little circle in the air. “Turn around.” She turned, so I could admire her from the back, looking back over her shoulder. I admired her, but I said, “I meant, twirl.”

She frowned, puzzled. She completed her turn so she faced me again. I said, “Twirl. In that skirt. Quickly, like a cheerleader.”

“Oh!” She spun so the skirt flared out and lifted. Her white panties and the sweet gap at the top of her thighs were exposed, then hidden as she came to a stop.

“Like that, sir?”

“Exactly like that. Good girl. You chose well. And no one else is to see you do that, you understand, except me.”

“I’ll twirl whenever you want, sir.”

I got up from my desk, and walked towards her. She stepped forward to meet me, and she kissed me again. I held her, and we pressed bodies together. “Now, little Jennifer, why are you here?”

“Sir?” It was too broad a question.

“In my office. After school.”

“Oh. Well, you wanted to see me in my new uniform, sir. Thank you, thank you!” I was holding her whole weight; she’d leaned into me with her hands around my neck, and relaxed.

“And you look perfect, Jennifer.” I kissed her, mouth to mouth, and she brought her hand up to stroke along my jawline. “And why else are you here?”

“I’m to tell you what I think about doing extra work for you. And taking extra… discipline.”

“Yes. You are. And what have you decided?”

“Of course, sir! I’d be so grateful if you set me extra work. I want to do better. And I know that if I don’t do my work right…”

“Yes.”

“You will make sure I do my best. With your hand on my bottom. Or worse. That’s as it should be, sir, isn’t it?”

“You’re a good girl, Jennifer. And of course I won’t accept anything less than your very best. I certainly won’t accept any excuses.”

“Yes, sir. I wouldn’t expect you to. Or want you to. I need direction, I know that.”

Note

This episode of Jennifer’s pleats and pleas is slightly ahead of time. When I left the Jennifer-and-Maddie-and-Lucy saga, Maddie was about to tell her headmaster about the time a girl called Lucy had go the cane for the first time, and licked Mddie’s cunt while she took that dozen strokes. That episode is still to come, but I’ve jumped ahead a bit, to where the story returns to young Jennifer Perch, and her adventures in the present. 

She’s discovering pleasures she’d never dreamt of, in one sense, while in another sense she’s dreamt of them for most of her life.

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.