Wicked Wednesday: Maddie’s virginity (last hours 7)

I kissed the tip of his cock [Maddie said], and it suddenly bounced up like a live thing that I’d disturbed. He made no sound, but he was shaking just a little, just like I was. I kissed that tip again, letting my lips enfold it. He gasped. So I was doing it right.

What surprised me was the softness. I mean it was hard, but the skin was soft, like it had peach fuzz or something. It doesn’t, but that was how it felt. I kissed it, and then opened my mouth to take him in a little more. So he couldn’t go flicking up out of my … reach.

“Take it, take me a little deeper, Maddie.” It wasn’t the voice I knew, that had commanded me when he’d spanked me, and that meant I couldn’t think of disobeying him. This voice was lighter. There was a constriction in his throat. He seemed younger. He needed me, and I could hear it. 

So I kissed that tip again, smiling. I liked it. I liked him. And I was in control here. Then I opened, and felt him push his cock in. He was trying to control himself, but he couldn’t help that forward movement, that first thrust, I was sure. I took his head, his glans, all the way in, and ringed my lips on him just past his foreskin.

I knew two things about how to do this. I licked the underside of his glans, and he moaned. Then I sucked, hard, my cheeks hollow between my teeth and he was silent. But his whole body shook.

He said, “Good, that’s good. You’re a good girl.”

Then I felt his hand on the back of my head, and he pushed me forward, slowly, until I had most of him in. I was a little scared. What if he rammed me forward, and I couldn’t take him all of his cock into me? Would I choke? Would he punish me? My bottom still burned, from the spanking he’d just given me. 

He said, “I’m going to move for a while. It’s called fucking your mouth. Now put your hand on the base of my cock. Good, that’s it. This way I won’t go too deep for you. It’s your first time, isn’t Maddie?”

I spoke to his cock. I didn’t want to take my mouth off it. “Yes, sir.” My voice sounded muffled. I was talking with my mouth full. If it hadn’t been so strange and so hot, I’d have thought that was funny.

“Good. Good girl. I’m glad I’m your first. Now, the next part is simple. I move in your mouth, and you suck. You suck hard. If you take your mouth off my cock, or I don’t think you’re trying, Maddie, I’ll cane you. Hard, and I won’t stop when you’re crying. I won’t bother counting, but you won’t get less than 50, across your bottom and legs. Understood?”

His voice had deepened again. Maybe I liked that voice better. “Yes sir!”

Then his hand pushed my mouth onto him, and he thrust forward to meet me, and I sucked him, hard as I could, as he’d told me. And he fucked my mouth, and the only sound now was my heartbeat, and my breathing though my nose, and his occasional gasps of pleasure.

Sometimes he pushed a little deeper, and although I had my hand on his cock, like he’d told me, I mostly let him. I liked that I could feel my bottom, so hotly punished, so swollen and burning, while I served him. 

We’d sped up. His cock was moving in my mouth fast now, and it wanted to get as deep as it could. It was like his body was controlled by some other force, not him. And I tasted something salty, and then he put his other hand to my cheek, trying to be gentle, and he said, “swallow every drop, girl, or you’ll get that caning.”

I was going to nod, but suddenly there was a spurt of salty, slippery stuff, hitting the back of my throat, and in less that a second my mouth was full of it. I swallowed, and swallowed, because I knew that if I gave him an excuse to cane me, in this moment he’d be merciless. Eventually I’d swallowed it all, I think, and his cock had slowed, still thrusting in my mouth but without the same urgency.  I followed my instinct and kept sucking, cleaning the shaft of his cock and swallowing my of his fluid, his sperm, as it came.

I wondered if I should stop, but he didn’t tell me to. So I didn’t.



Wicked Wednesday: Jennifer considers “feeling better”

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

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

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

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

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

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

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

Nude young woman applying lotion to her bottom

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

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

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

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

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

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

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

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

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

She laughed. “No, sir.”

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

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

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


Sinful Sunday: Don’t move till I’ve finished with you

No, girl, don’t you even think about getting up. 

There’s more? We’re not finished? 

Girl, I’ve hardly started.  


I want that ass nice and hot before I fuck you. 

Red hot?

Exactly. Blazing red, little girl. Like a firetruck, only fuckable. Now: get up on tiptoes. Good girl. And keep still. 

Even if it hurts? 

Of course it’ll hurt. And you’ll stay in place until I put the paddle down. Just do as you’re told, and you’ll be fine. 

Ummm, well..? Yes, sir.

Touch these lips for more Sinful Sunday submissions.


Wicked Wednesday: Jennifer’s pleats and pleas 8

I’d suggested to Jennifer that she might want to do a little more, to prove not just to me but to herself that she really was a good girl.

She seemed to accept the principle. But I expected some dramatic and florid ideas were passing through her head, while she tried to stare out my carpet.

“Well, I know a way, Jennifer. You fully earned that spanking you just got.”

I paused and gazed at her, so that she knew something was expected. After the briefest of pauses she nodded. “Yes, sir.”

“Correct. But you can gain some real credit with me, if you show you’re ready to learn discipline properly. I think you have some things to own up to, don’t you?”

Jennifer looked beseeching. She wanted to deny it, but I’d already shown too many signs of omniscience. She looked from side to side, then said, in the quietest voice imaginable, “Yes. Sir.”

hand-skirt2“And, you know, you can take punishments that you haven’t earned yet. So that things can be a little easier for you when the time comes?”

She frowned, considering that. It seemed to make sense to her, which, frankly, it didn’t to me. Her thinking was being influenced, as it should, by what her pussy wanted. I said, still very seriously, “That could mean additional spankings, or maybe the strap.”

She looked at me, her face back to its natural color. Something in her had relaxed. I said, “Do you know what a tawse is?” She looked blank. “No, you wouldn’t, I suppose. Anyway, those are options. Think on it.”

The bell rang.

“Ah, end of the first period. You’re done now. You’d better get going — I know you won’t want to be late for another class.” I let the smile get through, this time. I mouthed, silently, the word, “Or.”

She smiled back at me. The ideas implied by that “or” had pleased her. She stood up then, and I walked her to the door, as if she were a parent. But just before I opened the door that led from Maddie’s office to the corridor, and freedom for Jennifer, I touched her back lightly.

hand-skirt1She stopped, perhaps wondering if I would drop my hand to comfort her hurt. Instead I whispered into her ear. “Do think about earning that extra credit, Jennifer. It will be good for you.”

She flushed again. “Yes, sir.” And so I lowered my hand and cupped her left buttock. It was a caress, and she leaned into my hand, liking the contact while not wanting to admit it was happening.I let my hand drift over to hold her right buttock. She was perfectly still, not even breathing. 

After a few soft, sweet seconds I made it a smack. Affectionate, but more like a headmaster’s punishing hand. I smiled at her, and she tilted her head up at me. The idea that we should kiss hung in the air.

Then I opened the door, and patted her bottom one last time. “Hurry to class, now, girl.”

She walked out into the corridor, not looking back.

The photo-copier started again. Maddie had been listening. I frowned. She and I would have words about that. I shut her office door and, after a second’s consideration, locked it. Then I walked over to the photocopy room.


Wicked Wednesday: Jennifer’s pleats and pleas 7

Jennifer couldn’t believe that she’d thanked me for spanking her, but her words still hung in the air. Her face blushed as furiously as her bottom. She squirmed, and her little skirt rode up to the tops of her thighs, exposing that white-cotton gusset between.

The squirming was ... hypnotic

Jennifer’s squirming was … hypnotic

She’d have to stand up to pull the skirt down, and she knew she didn’t have permission. She couldn’t imagine asking for permission. So she could only blush, sometimes looking down and sometimes staring, uncertainly, into my eyes.

I smiled at her. “That’s better. The thing is, Jennifer, you’re a good girl. Really.”

I looked at her. Jennifer was still blushing furiously and trying hard to keep still. But she nodded. She was a good girl.

“Now, you get very good marks, Jennifer.” She squirmed again, her little pussy again flashing whitely between plump thighs. It was the word “marks” that had set her off. I said, “You have a very good record. Your marks, yes, your marks, are very good. You’ve won awards, and you take part in extra-curricular activities. It’s quite clear that achievement is important to you. Isn’t it?”

Jennifer closed her knees tightly. “Yes, sir.” 

“Good. Now, you’ve got a clean slate as far as I’m concerned. You did wrong, you took your punishment bravely. And now there’s nothing on your record. What do you say?”

“Ummm… Thank you, sir.” 

Mr fucking Scary, that's who

Mr fucking Scary, that’s who

“Good girl. Though if you’re late again, I’ll cane you. That’s fair warning. But you, Jennifer, you may be thinking that one spanking isn’t enough to make things right. Not in your own mind.”

I looked at her. Her hands were white. Her thighs trembled, knees slightly apart. It was as though I was looking at her half-naked again. I laid down a card. “In fact, you might prefer to go above and beyond to impress me that you really are well behaved. Wouldn’t you?”

She frowned. I was right, but she hadn’t expected this. “Yes, uh, yes, sir.”

“But you might be at a loss as to how to do so.”

Jennifer watched me, fascinated. Then she nodded, and looked at my carpet again. She’d seen a lot of it, in the last half-hour.



Wicked Wednesday: Jennifer’s pleats and pleas 6

Jennifer had her side to me, hands hovering about the hems of her panties. She’d seen herself in the glass of my cabinet, and the glowing red of her bottom had embarrassed her. Confused, she turned to face me, panties still around her lower thighs. Her face flamed redder, once she’d forgot the warm ache in her bottom for long enough to realize the vision she was presenting me with.

Her eyes asked me the question. I said, “Yes, you can pull your panties up now, Jennifer. And let your skirt down. It’s over, girl. For now.”

A costume drama: a moment of hesitant modesty

Costume drama: a moment of hesitant modesty

I picked up the wooden chair I’d been sitting in while she was over my knee. 

I put it back in the corner, and turned in time to glimpse that perfect little pouch, snugly cased in white cotton again, before her skirt dropped, cutting off that vision.

Like a curtain falling. The show really was over.

I sat in my office chair behind my desk and watched her.

She had her eyes on the floor while she fumbled her jacket back on. For a second she hesitated over the buttons. She was feeling naked, exposed. She thought better of it and dropped her hands to her sides. The silence lengthened. Eventually she looked up and met my gaze.

“Better,” I said. “Now. Have a seat.”

She was startled. She’d thought this was over and she’d be allowed to retreat. For some reason she raised her hands to her tousled hair, horrified about something, but she dropped them again.

She said down on the leather armchair I used for interviews with parents and, it seemed, just-been-spanked girls. She sat, the skirt halfway up her thighs. then shifted slightly. The skirt rode higher. Even a soft chair was reminding her that her bottom was sore, and the cool leather was contrasting with the heat of her bottom and upper thighs.

I was sure she’d remember that detail, perhaps tonight, one-handed and wet-fingered in bed. Lying on her stomach, I imagined her, bottom rising and falling while she gasped and moaned. Until she froze, arched, then moved again, spasmodically, as though she were being kicked. I wondered what her orgasm noise was like. I realised it was on my fucket-list: I wanted to hear that moan for myself.

I said, “So, Jennifer. You’ve been spanked for some very stupid behavior. Thinking you could get away with cutting classes. That was stupid. But you’re not stupid. So why? Do you like getting spanked?”

That was a dangerous question, pretending innocence. She pretended too. Mouth slightly open, eyes wide open, shaking her head. I repressed a smile.

I considered asking, “Are you sure?” To watch her denial some more. But the comedy was good as it was. “So that’s the skipping classes dealt with. Right?”

She nodded.

“So you thank me for your lesson.”

“Sir? I – “ she stopped. Swallowed. “Thank you for my lesson. S-sir.”


Wicked Wednesday: Jennifer’s pleats and pleas 5

I stroked Jennifer’s bottom and slim flanks gently, enjoying the heat radiating from her apple-red buttocks and the upper slopes of her thighs, and the relative coolness of her mid-thighs where her panties were bunched. I patted her hot little bottom again, because it was irresistible, then squeezed her. She sighed. She liked being under my hand.

What was I going to do about this? Jennifer would do whatever I said. Without limit, I knew that. But although something had become personal between us, very personal, I still had to protect her and her interests.

Hot, he thought. Wet. Submissive. One, perhaps two, strokes of one finger and she'd be his

Hot, he thought. Wet. Submissive. Confused. One, perhaps two, strokes of one finger and she’d be his

I continued to caress her gently while she stayed in her dreamy space. And I thought. I was sure she didn’t do any thinking at all. She’d been close to orgasm. So close that when she was more experienced she’d be frustrated, but for now she knew only that she’d been in wonderland. She would make sure she returned. At last I said, “Right. That’s that. Up you get.”

Jennifer looked up at me, red-eyed. She’d cried a little. She’d also forgotten how to move her body. I lifted her carefully, one hand under her belly and the other raising her shoulders. She stumbled back to her feet, skirt still tucked above her waist, panties still at half-mast on her thighs. With a deep red glow of spanked bottom and thighs between.

I wanted to keep her, to have her stand with her nose to the wall and her hands on her head, decorating my room.

Waiting for me to call her to me, and tell her what to do. Hoping that what she had to do would end that yearning she felt. End it in explosion and fulfilment. 

I was aware of the silence from the photocopying room. Maddie was listening intently. Jennifer was watching me, wondering if she had permission to pull up her panties and lower her skirt. 

Life had to move on.




Wicked Wednesday: Jennifer’s pleats and pleas 4

I’d said, “Lift, girl!” because I wanted Jennifer to experience herself cooperating to have her panties come down. And I’d tugged down the hem so she knew her bottom was already bare. She would think of no reason to resist, though her mind would be racing.

I was already looking down at her skin, rounded and blotched with the confused red bloom left by my hand, with the occasional finger or thumb-print showing on the outer areas. And at her pale, currently trembling cleft, the sweet perineal folds, and the hint, the merest centimetre or two, of her vulva. Swollen, she was, and wet. I smacked her again, still holding the panties clear, so my hand landed directly on her skin. That was better. I was sure that Jennifer felt so, too. “I said lift, girl.”

She moved suddenly. She’d been entranced and the smack had woken her. Her hips pressed against my cock, which was mostly hard, and used it almost as a fulcrum to lift her hips free of my leg. One deft tug, and one shocked little cry from Jennifer,  was all it took.

She was naked from her waist to about halfway down her thighs. Her pussy was perfect, as I’d expected: pretty, pale-pink little pouch. Jennifer settled again, against my cock. If she noticed that I was now completely hard she gave no sign. Just the constant pressure of her hip.

Usually, in my post-spanking lecture I would tell the girl to make sure she remembered this punishment. But there was no danger of Jennifer forgetting. The little damp patch in her panties testified to that. She would remember, and she would be back, I knew.

jennifer-spankedI said, “mmmm,” involuntarily, partly at that thought and partly because of this beautiful vision, this bare-bottomed girl over my knee, holding my leg. She squirmed for me, beautifully, to escape my gaze and to give me more to watch. I wondered if she could feel my gaze, and if she knew how lovely she was. If it was her first moment of adult vanity, she was certainly entitled.

I had colour. I wanted more movement. I resumed her spanking, my hand tasting her softness and the heat of her. I coloured in the paler patches on her bottom, making the spanks harder, until she was moaning and squealing almost continuously. They were her anthem, the anthem of spanked girls everywhere. Her hip bouncing against, caressing, my cock while she moaned. Her anthem: and I was standing for it.

I groaned, then fought for control. It was all I could do not to come. But her hips stayed pressed against me, rubbing me harder while I spanked her harder. I was sweating with the effort of control. If I came, I told myself, I would resign. But Jennifer helped, unexpectedly. She stopped moving, even as I continued to rain smacks down onto her beautiful little bottom. She relaxed under my hand. Her head drooped towards the carpet, and her hands still touched my leg for comfort and balance, but her grip had loosened. 

I’d seen girls go there before. I continued with the spanking, not varying the rhythm or the intensity. I envied her the place she had gone, but I didn’t want to wake her out of it. Now I was her lover, keeping her at her peak. 

Her thighs opened a little, microscopically, then closed; repeat. She started breathing more heavily, in the same rhythm. Oh. It wasn’t my orgasm I needed to worry about. I stopped the spanks and left my hand on her bottom, and squeezed her affectionately, to break the trance. 



Wicked Wednesday: Jennifer’s pleats and pleas 2

“Ah, Jennifer,” I said, once she was in my office and I’d closed the door. Jennifer was a pretty girl. Dark hair, cut into a mop around her face. Pretty smile, I knew from memory, though she wasn’t smiling now. She was trying to look calm, but her left hand was clenched, her nails worrying at her palm.  

She’d done up the second to top button of her blouse, to make a less immodest display of her cleavage, but she hadn’t been able to do anything about her skirt. It was cut high at her thighs, several smooth, feminine inches above the knee. She stood about five foot nothing, which underscored the voluptuous promise of her bottom, and the slender womanliness of her thighs. 

All I had to do, if I wanted to inspect that “genital pouch” that had provided Jennifer Perch with her school nickname, would be to tell her to put her hands on her head. The skirt would rise two inches, and that would be all it took.

But those were my thoughts, which I couldn’t do much about. In practice I’d have to tell her she couldn’t wear her school uniform skirt that short. That would make a lot of the boys less happy, but it had to be done if Jennifer was going to succeed at school at all.

I’d been tempted, when I’d paddled Jennifer’s two classmates yesterday, to make them take off their skirts as well as lower their panties. They’d kept slipping down, and I wanted to make sure my reputation as a ruthless disciplinarian was well established. But with Jennifer that would be unnecessary. Once she was over my knee, that skirt would give little more protection than a pleated belt. 

I looked at her. She couldn’t meet my gaze. She looked past me, at the row of certificates behind my desk. “Sit down.” I indicated the straight-backed wooden chair.

Terrifying headmaster, with tawse. And is he really a Pogues fan, or does he just like rum, sodomy and the lash?

Terrifying headmaster, with tawse. And is he really a Pogues fan, or does he just like rum, sodomy and the lash?

That chair, as I suspected Jennifer knew the moment she saw it, was going to play a major, dreaded, part in her life for the next few months.

She was a little short to be able to bend over it and rest her head on the seat when I paddled or caned her. But she could bend over facing the front of the chair, holding the seat for support.

She could lie over the seat, fingers and toes to the floor, flopping like a mermaid out of water when the tawse landed on her bottom.

In the meantime she sat on it, hands together and not still, staring at her knees.

She knew why she was here. She’d skipped classes, and she was to be punished. She blushed suddenly, and her knees drifted further apart.

The movement sent my imagination racing again. I could, once she was used to discipline, have her wearing only her shirt, sitting backwards on that chair, bottom extending past the seat, projected and unprotected into the air, with her thighs open and straddling that hard back.   

I asked the question I always ask. It gives the student a chance to confess, and if they do, as a matter of honour I will halve their punishment. “Do you know why I called you in to see me?”

However, confession hardly ever happens. Jennifer was no exception. She couldn’t look at me. I guessed she was still a bad liar, and I intended to preserve that state. She shook her head. A lie, but at least she couldn’t speak it. 

“When I started at this school, I familiarized myself with the files of some of the more noteworthy students.” I stood looking out the window now. “Your file stood out: straight As, awards. You’re an accomplished young lady.”

She made a sound, a bit like a grunt. Her high achievement seemed to embarrass her. I would fix that. She was about to have other things to be embarrassed about, and discipline would get her focussed again. It might help her to feel special. She needed that. 

I didn’t look at her. She was looking about my office, I was sure. “So I was surprised, Jennifer, when I checked the attendance records of your classes and found that you’d been skipping some of them. That seemed out of character.”

Now I looked at her, using all of my height, such as it is. I saw the beginning of a smile. That had to be extinguished, fast. “You’re only harming yourself with that behavior. So now we’re going to correct it.”

She was silent. She remembered the two girls from yesterday. The paddle on bare skin, and the dramatic results. Was that about to be her?

“That’s very much for your own good, when you’re behaving like a silly, naughty child, and you’ve finally been caught, wouldn’t you agree?”

“I guess.” Her voice was dry. But she was still trying to be nonchalant. 

“The correct answer is ‘Yes, sir.’ Try it.”

She wasn’t looking at me. “Yes, sir.

She couldn’t have packed more insolence into those two words if she’d had drama lessons. But she would mean it, by the end of our session today. “You know your behaviour has to be punished, Jennifer. Skipping classes is foolish and childish so your punishment will be too. I’m going to give you a spanking.”

Now she looked at me. Her mouth dropped open, her eyes wide. 

“I mean now, Miss Perch. Stand up.”

I pushed the comfortable office chair out of the way, and brought out the companion to the one Jennifer was sitting on., wooden, with a high straight back. She hadn’t moved yet. I gave her another order, so she had a sense of orders backing up, of losing control. “Take off your blazer.”

Still nothing, except furious blushing. I spoke sharply. “Or would you rather have the paddle? Over my desk like your two friends yesterday?”

She didn’t want that. She stood up suddenly, and took off the blazer. Folded it and draped it over the back of her chair.

“Wise choice. Now come here.”

She did. She stood in front of me. Her knees were shaking. “Please don’t spank me, sir. I’ll do extra work. I’ll … write an essay. Or clean all the blackboards. I’ll be good, I promise! I – I’ve never been spanked. Never. Please, sir.”

There was a sound from the photocopier room. Maddie was listening. She wouldn’t have expected Jennifer to beg. Jennifer looked over briefly, then switched her attention back to me. She was near tears. “Sir? Please don’t. Please don’t spank me.”

I smiled at her and shook my head. I patted my right thigh. “Over my knee.”