Maddie’s virginity: Post-mortem

“It’s nice that you’re holding me,” Maddie said. “I appreciate that you do care about me. You sadistic bastard.” I pinched her nipple, hard. “Ow! No, seriously, I do like it that you care about me. May I rub, sir?”

“No. I meant to hurt you. Stay where you are and hurt, Maddie.”I resumed the pressure on her nipple, a little harder.

She nodded. “Thank you, sir. And I do love that you’re cruel, and that you care about me. But I didn’t tell you that story so you’d sympathise with me.”

I let go of her nipple then, getting a gasp of pain from her. Then I rubbed and pressed it soothingly, since someone had to. “It’s a parable?”

“Yes. I don’t mean, watch out or someone will rape Jennifer. I’m not being that exact. It’s just that I think it’d be a pity for you and a tragedy for her if you both missed out on having each other.” She laughed. “Together! For the first time!”

I tweaked that nipple again, in warning, and cupped her breast with my hand. 

“Mmm. But I worry that you and she will miss out on something that would be very special.I don’t know.”

I kissed her. I had nothing to say. But she did need to know she was held, and loved. She relaxed into my arms this time, and there was a moment when it seemed she would roll back, pulling me down on top of her. But she drew her head away, and looked into my eyes. 

“I just want to say there are a whole lot of things that can go wrong in the universe. Jennifer’s eighteen. And she’s very horny. Horny for you, sure, but she’s also just horny in general.”

“What makes you say that? I mean, horny for me, specifically?”

“I watched her leave, the last time you spanked her. She was absolutely … blissed out. I know we’re not the same person, Jennifer and I, but I do know, close enough, what she’s feeling. Because I’ve watched her and heard her, and I’ve been exactly in her place.”

“True enough.”

“I promise you, from experience as well as observation, she wants you to show her how sex works, to make her undress for you so you can hurt her. She wants to be disciplined. It’s sexy and hot, and it makes her feel singled out. It make her know she’s special.”

“Well, she is.”

“So she should be. Sir. She wants you to spank her again, soon. Tomorrow would be good. And she wants the cane. Well, it’s more that she wants to experience the cane. To be a girl under your discipline. And, a little later but not too much later, for you to take her and teach her.”

I said, “So. I want you to make an appointment for Miss Perch to see me after school tomorrow. That should help her to feel singled out. And special.” 

“After school tomorrow, for Jennifer. Spanking or the cane?”

“Don’t know. I’ll ask her teachers how she’s been behaving. That will decide it. Probably a spanking. With a warning that it’s the cane next time.””

“Watch her make sure there’s a next time. And soon. And after that you should definitely fuck her. She’s longing for that to happen. She’s impatient.”

I nodded. I’d felt that too, about Jennifer’s reactions over my knee. “And I should make it happen.”

“Yes. Soon. And you should make sure its special.”

“Um, Maddie. What happened to you, when you knocked on the door? And he let you in and saw you? All messed up, my poor girl?” 

Maddie drew in a breath.

Wicked Wednesday: Maddie’s virginity (not long now)

Kate Winslet’s robe goes down, on the Titanic

“But,” Maddie said, “I collected every bit of courage that I had. And I said it. I said, ‘Sir, please cane me, and then afterwards, please fuck me.’

“And he smiled at me, so that I felt like the most blessed girl in the world, and said, ‘Thank you, Maddie. You asked very prettily. And yes, yes, girl, I will.'” 

I said, “That sounds good.” Maddie and I were lying together on the mattress in the store room. Oddly, I’d just caned her and fucked her myself, not so long before.

We were both lying on our backs. I leaned back on a collection of pillows, and Maddie lay back on me, her head nestled in the crook of my arm. 

Maddie turned her head and kissed my chest, not so far below my nipple. “It did. It sounded so wonderful. I was in heaven. But don’t forget, sir. This is a cautionary tale. It’s why you should take Jennifer soon. She wants you to. And if you hold her off for too long, there’s a real risk it’ll all go sideways. Or down, like the Titanic. Jennifer should have her fairy-tale. I’m afraid I didn’t.”

Leo takes down Kate’s particulars, on the Titanic

I said, “Oh?” I’d forgotten that Maddie was telling me this story so that Jennifer wouldn’t have the same fate Maddie had had, at Jennifer’s age. Therefore this story didn’t have a happy ending.

“Yes. Oh. As in Uh-oh. So I danced out of his office, so happy. And although I knew I was going to get the cane straight after school, I was looking forward to it.

“I figured it would hurt like his spanking hurt, in a lovely exciting way. And then his cock – I’d liked it so much when it’d been in my mouth. I knew I was going to love it when he took me. Not just my cunt, but my whole body. I was going to be his.

“I squirmed all afternoon. God, I remember it. I was so wet and so wanting. I was hotter and hornier than I’d ever felt. If I’d even got a breath of wind on my cunt I’d have exploded. I would’ve screamed the whole classroom down. Shattered the windows.”

Kate enjoys a good lie-down, on the Titanic

I reached down idly and tickled Maddie’s belly, then a little further down and stroked her cunt. She was eleven years older now than she’d been during the events she was describing to me, and soon to turn thirty.

She was every bit as wet as her younger self. Maddie sighed comfortably as my fingers sank into her. I pushed my fingers a little deeper, and she rolled her hips, nuzzling her cunt greedily against my hand.

I had an idea that Maddie was going to need comfort after she’d finished her story. I kissed her. She kissed me back, but she broke the kiss first and turned her head away. “So, after school I went back to his office.” 

 

Note

I tell stories at a leisurely pace. If a thing’s worth doing it’s worth doing slowly, say I. So it’s easy to forget how Maddie’s story started.

In a deleted scene, after the Titanic has sunk, Kate learns to walk on water and saves herself, Leo, and the wooden panel. Certainly, it was a night to remember

Maddie’s lover, our narrator, has admitted that he has the desire and the duty to initiate his student Jennifer Perch into certain adult pleasures. Maddie tells him her story to advise him that he should make sure he looks after Jennifer properly and make sure her first sex is happier than Maddie’s had been.

So I’m foreshadowing that the next episode (or more, given the speed at which I tell stories) will be realistic rather than pornotopian.  

But don’t worry too much. I can say, without giving too much in the way of Spoilers, that there are happy endings all round, in the past and in the present.

Wicked Wednesday: Maddie’s virginity (last hours 9)

Maddie lay beside me on our mattress in the storeroom. Her head in my shoulder, staring at the ceiling, she told me the story of the end of her virginity.

She’d just told me that after being spanked by her headmaster, she’d sucked him off. Once he had his cock back in his pants, he’d said “Good. Now, stand up, Maddie.” 

I’ll let Maddie tell it, from here. 

Maddie’s story

I said, “Yes, sir.” I had to put my hand on the floor to steady myself. But I stood in front of him, my eyes at his chest. He was so close to me, and I wanted to hold him. But I waited for orders. He smiled at me. 

“You’re such a very good girl. You know you have to come back here after school.” 

It was a statement, but I said, “Yes, sir.” 

“And why do you have to come back?” 

“I was late, sir. And you’re going to punish me.” 

“How am I going to punish you, Maddie?” 

“You’re going to cane me, sir. Cane my bare bottom. Like that boy.” 

“That’s right, Maddie. Or nearly right. I didn’t undress him, not completely. You, on the other hand …” 

I’d hoped that. It seemed so daring to think I’d be naked in front of him.

I’d already been more daring than that, but being naked for him would be a new thing too. My legs trembled. It wasn’t fear. “Oh, sir…” 

“And you just made me feel extremely good, Maddie. Would you like to feel good after I’ve caned you?”

“Oh, please. Yes, sir.” 

“Good. Then ask me. Say: Please cane me. And then please fuck me.” 

I opened my mouth. Then I hesitated. It felt like he could already see me naked. I felt so shy.

Wicked Wednesday: Maddie’s virginity (last hours 8)

I stayed on my knees [Maddie said], suckling the headmaster’s cock as it softened in my mouth. His hand in my hair no longer gripped me quite so tight.

He’d meant it to hurt while I pulled my head forward to take all of him into my mouth. Now it was a caress.

Eventually it was soft. It still felt huge in my mouth. I kissed it one more time, as he finally withdrew. I knelt before him still, not knowing quite what to do.

His taste was still in my mouth. I wondered if, back in class, people could smell it only breath.

He smiled down at me.

“Good girl, Maddie. That was very well done. I’d never have guessed it was your first time. I think you were made for this too, don’t you?”

“Oh my god. Yes, sir.” I liked that he thought that. For him I’d stay on my knees forever. I was in my place, where I’d always longed to be, even before I knew it. And I liked that I was the place he wanted to put his cock. 

“Oh, yes, sir!”

When I was a little girl I’d always enjoyed chances to please my teachers. I’d clean blackboards, But it made me feel singled out. I took his cock, kissed it reverently one last time, and tucked it back into this underpants.

It showed signs of life again. I smiled up at him. This cock: it was going to be properly in me this afternoon. After school. After he’d caned me for being late.

He smiled back. I zipped him up, and rocked back a little, still on my knees. I felt special. His helper.

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: Maddie’s virginity (last hours 6)

“Come here.” 

I rushed to him, and I couldn’t stop. He caught me and folded his arms round me. I lifted my head up and he kissed me. I kissed him. He had a strong face, with the stubble coming through. His breath smelled of mint. It felt so good. How long we stayed like that I don’t know, but then he stepped back just a little.

He started to undo the buttons on my shirt. I just look at him, longing, while he undressed me, took off my tie, and then the shirt. I was naked, except for my shoes and socks, and my bra.  

“Now turn round, Maddie.”

I did, and I felt him undo the bra and take it off.

Then he took my hands in his and pulled them together, behind my back. “Don’t move,” he said, and he tied my hands together, behind my back, with my own school tie. I gasped, wide-eyed with the wonder of that. I’d been helpless before anyway, but to be tied was a whole new level. He didn’t need me to choose to obey him, now. I was at his mercy. My cunt felt … empty, wanting. I needed his fingers back, or better yet his thing.

Then he smacked my bottom. I gasped. I was so tender there, and the smack re-awakened all that soreness. He spanked me another five times, without speaking. I trembled, trying to hold myself still for him. 

“Now get down on your knees, Maddie. You know why, don’t you?”

“Oh yes, sir!” So, he was going to let me suck his cock. I’d heard girls talk about feeling a boy get more and more excited and then spurting their salty stuff into their mouths. Then they’d swallow it. I wondered what he’d taste of. 

I crouched as low as I could, then fell forward onto my knees. It was awkward with my hands tied. My face was level with his …

I watched him unzip. I’d hoped he was going to take his pants off, but it seemed that I was only going to be allowed to touch his cock. I leaned forward, to kiss it through the material of his pants. 

He let me for a few seconds. Then he pulled my head back, with his hand in my hair. He made an adjustment to his pants with his other hand and suddenly there was his cock. It was the first I’d seen. Except for my brothers after a shower, when we were very young. 

But his cock was very different. It seemed huge, and it pointed straight at me. It wanted me. It needed me. I leaned forward to take it, and my hair pulled, because he’d neither let go nor moved his hand. I had to push forward, hurting my own scalp, so I could kiss the end. 

 

Wicked Wednesday: Maddie’s virginity (last hours 5)

I lay over the headmaster’s lap [said Maddie]. My bottom was still sore, really sore, from my spanking, and yet I was blissed out.

I’d come twice while he stroked my cunt. He’d had his fingers inside me!

I kept telling myself that, over and over, because it was such a strange thing, and so wonderful.

It meant he’d wanted me as much as I wanted him. He’d looked after my pleasure. No one had ever done that for me before. 

I was his. If he’d told me he wanted to cane me I’d have taken off the rest of my clothes and bent over for him. If he wanted to fuck me I’d have aid on my back or own my front, on the carpet or on the desk, whatever he wanted. If he wanted me to suck his cock I’d have knelt for him, and let him into my mouth. I’d never sucked a cock before, but I’d heard other girls talk about it. I knew he’d teach me the rest and make sure I pleased him. That thought made my rock myself across his lap. I moaned. 

He put his hand back on the bare skin of my bottom. His touch was so cool against my burning skin. “Maddie? Are you all right?”

“Thank you, sir. Thank you for my spanking. I needed -” I thought about how to say what I’d needed, and I chickened out a bit. “I needed you to make me behave.” 

“Yes, you did.” But he sounded amused. He knew I’d started to say something much more personal. “Well, we should make sure you get what you need, shouldn’t we?”

His hand started to rub little circles on my left cheek. I sighed. It was so lovely. 

“I hope you do, sir. And …” I lost my nerve. 

“And what, Maddie?” His hand pressed down on my bottom: a warning. He could repeat my spanking easily enough. 

“And is there, is there anything I can do for you, sir?” My heart beat hard, once I’d said it. I was offering myself to him. What if he didn’t want me?

His hand slipped down again, and he caressed my cunt. Just along the lips, over and over, getting his fingers wet with me. I’d spread my legs for him as far as I could, and now I crawled forward a couple of inches and lifted my bottom so he could watch my cunt as he stroked me. I could feel his cock pressing against my hip. It seemed to be trembling. He was throbbing, with desire for me. 

I said, “We’ve already broken all the rules, sir. And I want to.” It was the bravest thing I’ve ever said. 

“Yes,” he said, after a pause. A long pause while my world hung in the balance. “You can close the curtains for me.” 

I felt a second’s disappointment. He wanted me to re-organize his office? Then I realised what he meant, and I could have sung. I got up, making no attempt to cover myself, and closed the curtains. There were people out there, playing basketball, but no-one was looking at the offices. 

Then I turned to him, naked from the waist down and knowing that he liked everything he saw. I said, “Sir?” 

Note

This is one seriously unethical headmaster. Both headmasters in this story belong in the bar-y place, the stripey hole, the jewel-case of infamy.

I found the scenario incredibly hard to write at first. It originally started as an agreement to write the male perspective on a story that appeared in the Sex is my New Hobby blog. 

But Zoe stopped writing her story, and this has gone off in other directions since then. 

But I don’t feel quite as uncomfortable with the wicked teacher/naughty schoolgirl scenario any more.

Like Christian Grey, the man in this story has no idea of what ethical consent might be, or why you shouldn’t do anything without it. (He has her consent, but there’s no way it’s ethical.) So the events in this story should not happen in the real world, just like Christian Grey shouldn’t strap his girlfriend without informed consent,

I won’t talk about the obvious fact that the 50 Shades books are badly written. I’ve mocked them before. Now I’m only saying that Grey is a a lust object for some women, and he’s not a role model. for anyone  

Mr Grey’s Amazing Shades. He has another 49 pairs.

But during some discussions about Mr Grey and his Amazing Shades, I came to agree with the women who skipped most of those books but read the spankings and fuckings.

If he’s a character in an erotic story, a fictional character isn’t obliged to be ethical. He’s just obliged to be sexy. Taboo or no taboo. 

There is a sense in which the headmaster, rather than Maddie, hot girl though she may be, is the object of desire in this part of the story. 

POV

By the way, this is a story within a story. The main narrator runs the school where Maddie works as a secretary. Maddie is telling him the story of how she came to lose her virginity, back at the school she attended. And he is reporting to the readers the story that she told him.

So although it appears to be female POV, it’s filtered somewhat by the version of what she said that her employer is giving. 

(And all of them are characters made up by me. Though I’ve known people similar to Maddie, and bits of them keep getting incorporated into her. I have a sense of who Maddie is, and she’s started to feel somewhat real, to me. So I’m trying to be true to her, as best I can.)

Wicked Wednesday: Maddie’s virginity (last hours) 3

So I was lying over his knees, bottom bare, waiting for his next touch. I knew it wouldn’t be him stroking me between my thighs again. He wanted to hurt me. It was his duty to punish me. I knew I’d been a brat to my teacher, really, and I couldn’t say that I didn’t deserve it. But with the headmaster instead of my teacher, it was a whole different experience.

He’d said, “you’ll come over my lap”. It hadn’t been what he meant, but I knew that I would. And that he wouldn’t be shocked. I could feel his thing hard and pressing up under me. He’d know, and he’d like it.

[Maddie and I were lying side by side on the mattress in the storeroom, her head nestled under my arm, while she told me this story. She’d started idly stroking my cock while she talked.]

I wriggled a little until his thing was between my thighs. I was sure it got bigger. Anyway, I know this was how we both wanted it. For now. We wanted more, too. My throat was so dry. We were nearly doing it right now, and I was sure that when he made me strip completely, to get the paddle, we couldn’t resist. He’d take me.

He was so handsome, and so dominant, and so good to me. I wanted him to take me. He should be my first. Someone who knew what he was doing, and wouldn’t hesitate. It was only right. 

And then his hand landed, on my left cheek. It felt so hard, and made me feel so soft, under him. I suppose it should have hurt, but it didn’t. It was like the strap on my hands, only a thousand times more. It felt like fire. It felt like sex, not that I knew that then. 

But I wiggled, part from reaction, and partly to keep his attention. I knew I was going to leak soon. I’m a juicy girl. 

[“I can confirm this”, I said, and she kissed me. She said, “Shhh. For now.”]

And his hand landed again on the same place. It sounded louder, so it must have been harder. But it just felt like a caress.

My skin tingled, and so did my cunt. I went wiggling again, and he grunted. His moved, while I lay across his knees. He couldn’t help himself.

His cock needed the release. I knew it. He was mine. I was so happy I could have sung while he spanked me.

He spanked me again on the same spot, his hand so hard, so firm above me; his cock just as hard and firm below me. It was fire and sweetness. And I could feel myself running, juices running down my inner thighs. He’d been right when he’d said he’d need a towel when he spanked me. But I was glad he hadn’t. I didn’t want anything at all between us. I moaned, and he couldn’t possibly have thought it was from pain.

He switched to my right cheek at last, his hand landing, hard. I worked myself on his thing, hips rolling up and down, while he added two more hard smacks. I loved the feel of his hand. I suppose it did hurt, in a way, but there were so many other things it made me feel that I barely noticed the pain. It just wasn’t what was important.

After the third smack on my right cheek he stopped. I suppose he was looking at me. Then I felt him again. My touched my cunt! Directly, with no pretence that he was doing it accidentally. I nearly screamed. I said, “Please…” Though I’m not sure what it was that I was begging for.

He said, “good girl.” And then his fingertips pushed into me. 

My mouth and my eyes were as wide as they can go. It felt so incredibly sweet, and right. My own fingers had been there before, but no one else’s. He knew what I wanted, and he pushed further inside. I moaned from pure pleasure, though I was trying to keep myself quiet.

His fingers pushed hard into me, and withdrew slowly. I stopped moving, my bottom up, splayed for him as wide as my thighs would go. I could do the splits, then. He grunted. “Wet girls need spanking, don’t they?” 

 I could hear the smile in his voice, but my answer still mattered. The cane and the paddle weren’t so far away. “Yes, sir! Wet girls deserve anything you want to give me. I mean, them.” 

He laughed, and this time he withdrew his fingers all the way. My cunt felt bereaved. Bereft. But he rested his hand on my bottom. “You’re right,” he said. And then the spanking started again. 

This time it was harder, and I understood that before he’d been going easy on me. These smacks were hard, and fast, and absolutely relentless. I lost count early, and they just kept coming. The pain was there. I still felt that sweetness, but now I had to admit that he was hurting me. And that I wanted him to. 

Sometimes he’d stop suddenly and hold me still. just for a few seconds. I knew he was having trouble stopping himself from coming. I wanted him in me when he came, so that suited us both. Each time he stopped, he spanked harder when he could move again. Something strange was happened. It felt so glorious, but I found myself crying. Just a couple of tears running down my cheeks at first. But soon, his hand still regularly smacking onto my flesh, my tears flooded, My mouth opened and I cried like a baby. 

I think he liked that. He stopped and stroked my poor needy cunt again. From the inside. Very firmly, but very slow. Something was happening in my body. My toes curled, inside my shoes, and my stomach muscles tightened. Then this wave of sweetness, of absolutely joy hit me, and I – well, I dissolved in it. I came, and I screamed and wailed, and I couldn’t help it or make myself quiet. It was the most wonderful thing I’d ever felt.

I lay drooping across his lap, hands and feet resting on the carpet. He held me in place, and kept stroking me. I thought I was spent, but in less than a minute I felt a second wave. Not quite as big or terrifying, but warm and satisfying. He stroked a little longer, but I was done for now.

I knew there’d be more of that feeling after he’d paddled me. I wondered how his thing would feel, inside me. Or would he just use his fingers? I didn’t mind what he did. I felt utterly blissful. For now I was content to wait. I was content in every way, come to that.

Wicked Wednesday: Maddie’s virginity (last hours) 2

My teacher kept me after class, the bitch. [Maddie said, as we lay together in the storeroom.]

She was taunting me, knowing I was desperate to leave. She asked me how many strokes I’d had on the hand, and whether I’d been paddled before. She was watching the clock the whole time. She let me go at 12.03. She chose that because she knew I’d have no chance of making it to the head’s office by 12.05, as he’d instructed me, and that if I had two minutes I’d try anyway. 

So I ran, staying out in the playground and not in the corridors, so as not to get in more trouble. When I got to his office, I made it 12.07, so that was it. I was in for a return visit after school to get the paddle.

But then I thought that maybe his clock might be slow, and he wouldn’t notice I was late, so I knocked at the door.

Then I heard a sharp noise, like a pistol shot, very loud, from inside. Then, half a minute later, another one, and another one after that.

Someone was being punished. Punished hard, by the sound of it. But was that the paddle or the cane? Was it a boy or a girl? Then there was a fourth stroke, and I heard a gasp of pain. So it was a boy, trying not to cry out, and not quite being able to stop himself. 

I heard the headmaster roar at the boy that he was to take his punishment in silence, and that he was going to get that stroke again. Then there was a silence, and in a moment, the headmaster opened the door. 

“Hello, Maddie. You were two minutes late. You’re a glutton for punishment, aren’t you?” 

I said nothing. There was a boy – well, really a young man, in the same year as me, so he’d be 18 = bent over the desk. His pants and underpants were round his ankles. The head had the cane in his hand still, and there were maybe a dozen stripes across this boy’s ass. More. I’d never seen cane stripes before. I’d never seen a boy’s bare ass before, come to that. I was a shy girl, then. So I gawped, open-mouthed. 

The head took my arm, and made me kneel on a chair, hands on head, nose to the wall. “Yes, you are a glutton for punishment, you silly little girl. Now, you keep your nose touching the wall. If I see your nose before I’ve told you you can move, it’ll be the worse for you, girl.” 

And with that he went back to his desk, and said, “All right, Rob. We’ll give you that stroke again. See if you can stop yourself from whining, this time.” 

Then there was the crack of the cane again, and the sound of the desk jolting when Rob’s body slammed against it. But he made no sound.

I wondered if I’d ever be able to take a stroke like that. It didn’t seem possible. And yet I knew that one day I would. For him. 

Then there were three more strokes, and Rob – I remembered him now; he played football, and was one of the popular boys – screamed. It was so shocking I couldn’t help myself. I turned to look. Rob knew he was in trouble for that scream. He was crying audibly, all his defences down.  

“Well, you’ve just made your caning longer, Rob. And I’m going to have to keep his nosy girl waiting for longer.”

I turned my face back to the wall, as fast as I could, knowing it would do no good. What did I think of seeing and mostly hearing Rob getting flogged? I don’t know, exactly. I was disappointed that it wasn’t just the head and me. But … I liked thinking of him doing that to me. And if he was caning me, would I like it if he let someone else into his office while I struggled not to cry out? I don’t know about the reality, but the thought of it was so hot.

He said, “Maddie. What are you here for?”

I thought. It was such a huge question. “I’m here for a spanking, sir.”

“A spanking. On…?”

I said quickly, “On my bare bottom. Sir. Uh.” My cunt felt it, when I said those words to him. “I’m here for a spanking on my bare bottom, sir.”

“That’s better. Now, Maddie, if you can’t give Rob his privacy, there’s no reason you should have any privacy either, is there, nosy girl?”

“Um. No, sir. I’m sorry, sir.”

“Good. So make yourself ready for your spanking now. The bare bottom one. Skirt off. Panties … not just down, for you. Right off. Now, Maddie!”

“Yes, sir.” I slid down from my knees on the chair, so my feet touched the floor. And I undressed for him. Knowing he was watching me. He’d seen my top half when he’d given me the strap. Now he was looking at the bottom half. I wondered if I’d be naked when he paddled me.

I looked at him. I didn’t dare put my hands in front of my cunt. He was the first man to see it. My heart was pounding, and I knew I was going to spill soon. I wished he was caning me. I wished I could bend over his desk, naked for him. So he could do what he liked to me, and then take me.

But I asked him with my eyes what he wanted. He said, “Back in the chair. Hands on head, nose to the wall. If I see your face again, before I call you, I’ll cane you, Maddie.What will I do?”

I remembered to keep my nose pressed to the wall. “You’ll cane me, sir, if I look again.”

“Good.” I heard him walk to Rob’s right, so the strokes would go the other way.

“All right, boy. Do you think you can take the rest of your punishment without any more snivelling?”

It took Rob a long time to answer. Eventually he sniffed once, loudly, and said “Yes, sir. I can take my caning without snivelling.”

“Well, you’ve done a pretty poor job of showing it. I’m not at all satisfied. I’m going to give you four now. And you’ll be back here tomorrow. Is that understood?”

“Yes, sir.” The voice sounded despairing. Then there came four loud cracks, mercilessly hard, and in quick succession. Rob jolted the desk under each one, but he managed to keep his mouth shut.

I heard the cane rattle on the table. “Right. Up you get, boy. Get your pants up. And, Rob -“

“Yes, sir?”

“You’re not to wipe your eyes. Go back to class and sit there till class resumes. But I want your teacher and your classmates to see what a crybaby you are. I’ll be asking your teacher whether you had tears on your face, so I suggest you don’t disobey. Understood?”

“Yes, sir.” There was resentment in his voice. I was shocked. How dare he disrespect Sir?

“I heard that, Rob. We’ll talk about proper, respectful speech tomorrow. Before I repeat your caning. Now, let’s try it again. Do you understand?”

Rob cleared his throat. “Yes, sir. I understand, sir.”

That was better. I actually nodded, pleased that he’d learned to respect Sir.

Then I caught a glimpse of Rob’s face. I hadn’t moved, but he’d stepped into my visual field while he put his clothes on. The look he gave me was pure venom. It shocked me. I kept staring at the wall, knowing he’d be staring at my bottom now.

“Get out, Rob. Straight to class with you, and no wiping your eyes. Or your cheeks. Go!”

Rob said, “Yes, sir.” He cleared his throat again. “Thank you, sir.” And the door closed behind him.

The headmaster put his hand on my shoulder. “All right, Maddie, you can get up now.”

“Thank you, sir.” I stood up straight in front of him, displaying myself. I wished he’d touch my cunt. Maybe rub me.

“You’ll come over my lap in a second. But I’m curious. Did you feel sorry for him?”

“No sir. Not for a second.”

“Why not, Maddie?”

“Well, sir. I trust your judgement. And anyway, I heard him disrespect you.”

He smiled at me. I noticed he wasn’t using his “strict” voice any more. He was kind again. “So you’re my little warrior, are you? On my side.”

“Oh, yes, sir.”

“Good. I’m pleased to hear it. One thing, though. He deserved that, every bit of it. And he deserves what he’s getting tomorrow. He’s a bad person; a bully, and worse. Maddie, I forbid you to speak to him. Or spend any time with him. That’s an order, girl. For your own safety.”

I said, “Thank you, sir. For the warning. And I will keep away from him.” Huh, I thought. That won’t be hard.

He sat down in the chair I’d been kneeling on, and patted his lap. “Come over my knee, Maddie.”

“Oh sir, yes!” That was a giveaway, but we were hardly bothering to pretend any more. I dived across his lap, pressing my cunt down where I thought his – Oh, there it was! And he put his hand down on my bottom, and rubbed and stroked me. I’d guessed right. It got harder, and pressed against me. I sighed. I was happy, here.

“Feet apart, Maddie. No, further apart. No, right apart, girl.” And his hand slipped down between my buttocks, and nearly touched me where I wanted. I felt so much need.

Then his hand was gone. “Arch your bottom up, Maddie. Lovely. Now we begin.”

 

 

 

Wicked Wednesday: Maddie’s virginity (last hours)

So I’d just told the headmaster I was made to be strapped and spanked. By him. Seems I have a thing for headmasters, don’t I?

[I squeezed Maddie’s shoulders as she lay back, nestled in the crook of my right arm. We were relaxing on our makeshift bed in the storage room next to my office. I was her current headmaster, and I’d marked her body well with my hand and the cane before we’d fucked. Though for me she was office staff, not one of the students. She was telling me how she came to end her virginity.]  

So he smiled at me. Because I’d said the right thing. And because he knew perfectly well that I wanted him.

No, I didn’t just want him. I wanted him to be as cruel to me as he could bring himself to be, before he laid me down, spread my thighs and made me feel – all the things I wanted to feel.

I wanted him to walk on me, to pull me around by my hair. I wanted him to slap me, and make me cry for him. I wanted his cock to stretch me until I was so filled up I’d think I couldn’t take him.

I gazed up at him. I must have seemed so serious. I knew he was going to throw me out of his office and back to class. I didn’t want to leave. My cunt was yearning for him so hard it hurt. My thighs were shaking. I could feel my own juices running down my inner thighs. It’d take me at least a dozen paper towels to make myself look normal before I could get back to class. I didn’t want the other girls to know what a weird little girl I was.

“Maddie, you’re to go back to class now. And tell your teacher that you’ve had the strap. And that you have to be here no later than 12.05. Or you’ll get extra punishment. So, girl, it’s time you were on your way.”

I remembered he was going to make me take off my skirt and panties before he spanked me at lunchtime. There’d be no hiding it then. I’d just be at his mercy. Somehow, I didn’t mind him seeing. I’d be flowing for him. He’d know what to do.

He stepped towards me. I was sure he was going to tell me, then, that he loved me and needed me. But he just put one hand low on my belly, and reached with the other to flip my skirt up and tuck the hem into the waist so it stayed up. He spanked my through my panties, six hard ones, while I leaned against his body.

His hand cupped my let cheek, and patted me more affectionately. And then it moved between my legs – I’d stopped breathing – and his fingertips touched my left inner thigh, high up so his fingers found all my slippery wetness.

If he hadn’t been holding me then, I’d have crashed to the floor.

Then he stroked me, a little further up, so there was just the most fleeting touch, just the edge of his hand, touching the wet cotton covering my cunt. It was so soft and so fast that I could have told myself it hadn’t happened. But it had.

He smiled again, and smacked me one last time. “If I’m to spank you over my knee, Maddie, I’m going to need a towel, aren’t I?” 

I suppose I must have blushed as hard as I ever have in my life. I nodded. Then I remembered and said, “I think you may, sir.”

He laughed, just a very little. And he smacked my bottom again, and led me to the door.

On my way back to class, via the changing rooms, I wondered why I wasn’t more worried about the spanking I was going to get at lunchtime.

Or the paddling I’d almost certainly get after school. But I couldn’t make myself feel that these things were scary. He didn’t mind that I was a wet girl. He didn’t mind that I was turned on. He knew I was weird, and he still liked me. I was sure of it. 

I knew it wasn’t just me who was made for this. He was, too.