Wicked Wednesday: Maddie’s virginity story 2


1 The previous episode is here.

2 I tried to work a wedding into this week’s effort. But it wouldn’t fit. I compensated by adding steam. 

Maddie’s virginity story 2

I was half excited [Maddie said], and half afraid. The Headmaster, his name was Mr Hunter, was a fox. Cool, sculpted smiling face, And he was sort of skinny, but in a cool way. You know, I thought he was older than he was – like Jennifer probably thinks of you – but I fancied him anyway. 

I knew he was going to punish me much harder than my silly teacher. That scared me, but I could feel that thought in my belly and in my cunt too. I imagined him reading the note: then he’d look at me, just the two of us in his room. And he’d tell me how he was going to punish me, and what I had to do to make my body available for him.

It wouldn’t be the same as making my body available for him the way I wanted most, the way I wanted him to want me. But it was still sexy. Unimaginably hot. I remember I was shaking, just from the desire I felt. It was like nothing I’d known before. 

I don’t know how long I waited after I’d knocked. It felt like forever, and then I heard him call, “Come in.” He had a lovely, deep voice, a take-no-nonsense voice. 

So I came in. He looked at me, then at my thighs. The way I’d hitched my skirt they were mostly on show, and they were shaking. I hope he liked them. I hope he liked me. Even if I’d been bad. 

He said, “Maddie, isn’t it? What are you doing here?” 

I said my teacher had sent me. I collected all the bravado I could manage and said, “I expects she wants you to punish me.”

I passed him the note she’d written. He read it while I watched his face, hoping to see anything like a smile or a twitch of humour. But he only frowned. He looked at me for ages – it was probably only a few seconds, but it seemed forever. 

Eventually he stood up. He said, “What are you expecting to happen now, Maddie?” 

I was meshing my fingers. I was still massively turned on, but I was getting scared too. “You’re going to punish me, Mr Hunter.”

“Sir will do for now, Maddie. All right. It’s clear to me that you like trying to make your teacher look silly. So I think I know where we’ll start. Take off your jacket and shirt, Maddie-”

“Sir! You can’t make me -“

“- So I can strap your hands. Ah, Maddie? You want to tell me what I can’t make you do? You’ve been given your copy of the school’s rules, I trust, Maddie?”

“Yes, sir, but -”

“Good. Because I hope you remember that not knowing the rules is a paddling offence. So, do you know your school rules?” 

“Y-yes, sir.” I was terrified that he’d question me on them. I’d read them once, and I don’t think I could have told him any of them.

He’d scared me into lying to him. He knew I was lying, too. But he just said, “so, according to the rules, who gets to decide what clothing a student removes, to prepare herself for discipline, Maddie? Me, or you?” 

“You, sir.” 

“That’s right. Now, because you objected, I’m going to add more strokes, of course. And – I trust that you’re wearing a regulation school bra, Maddie, and not some skimpy thing of your own?”

I was so lucky. My bras were in the wash, so I’d worn the school one that morning. “Yes, sir.”

“I’m astonished. But good girl, for that at least. So, you’ll take off the jacket, and the shirt, and the bra, Maddie.” 

I said nothing. I thought he was waiting for me to protest. Eventually I realised and said, “Yes, sir.” And I began to undo my buttons. I could see I had goosebumps on my breasts. then I put my clothes on the chair. The chair that was for girls who weren’t in trouble. (That was what I thought then. Yeah, I soon learned what chairs are for.)

So I stood facing facing him. He could get an eyeful of my goosebumps, I thought. But I was naked from the waist up and I knew that wasn’t really what he was looking at.

He looked at me, my belly and my bare breasts for ages, again. I wanted him to be pleased, but he showed no sign. 

I was so aware of my body. No man had seen my breasts before. My thighs were shaking again. And my cunt flowed.I could feel it, you know, spillage, running down my inner thighs.

“Good girl. Now hold your left hand out towards me. Palm upwards, and keep it flat, Maddie.” 

My mouth fell open. Oh god, I’d dreaded and wanted this. And here it was. 


The next episode is here.


9 thoughts on “Wicked Wednesday: Maddie’s virginity story 2

    • Well, to get to Maddie’s first fuck (which is what her story is about) will take another two, possibly three episodes.

      But the story is called “Jennifer’s pleats and pleas”. And if you click on that tag, at the bottom of the post, you can review all the episodes so far. It’s been a long, filthy journey, so far. (Started out with realism but soon hit the harder stuff.)

      And I’m sorry about the stop at the dramatic moment, but:
      1 it was getting long enough; and
      2 I like cliff-hangers.

      Thank you for reading! And even more for commenting!!!

  1. Pingback: Wicked Wednesday: The revised virgin (Maddie’s story) | Jerusalem Mortimer: Between the Lines

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