Wicked Wednesday: Maddie’s virginity (last hours 4)

The previous episode is here.

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?” 


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. 


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.)


The next episode is here.

9 thoughts on “Wicked Wednesday: Maddie’s virginity (last hours 4)

  1. Fiction is and should be, free of angst for the writer. Amoral characters are more common in erotica than mainstream fiction, because fantasy is easily recognized as such by the tone of the story. Being comfortable with a despicable character does not me that the author is one and the same. To draw a close parallel, murder mysteries are extremely popular, but don’t carry the visceral punch of true crime. The best fiction should make the reader at least slightly uncomfortable.

  2. Thanks for your thoughtful comment.

    I suppose I’m still a bit conflicted. I don’t think there’s ever likely to be a book called, “Hottest 100 Women’s Rape Fantasies”, because although it’s true that some women fantasize about rape, it’s still a topic where only an asshole would want to put out a book that could be seen as confirming the “they all want it/deserve it” discourse.

    True, the content of the rape fantasies that I’ve been told is very different from the sordid reality of rapes that actually take place in the real world. “Relentlessly sexy man doesn’t take no for an answer, delivers long, multi-orgasmic sexual experience” is not quite what life delivers, in terms of forced sex.

    So a rape fantasy is not really about actual real-world rape at all.

    And, if Maddie fucks her headmaster, that would be rape even though she’s utterly keen and even though she’s over the legal age of consent, because the headmaster is in a position of authority over her. There are good reasons why that headmaster (well, both of them; there are two headmasters in the Jennifer/Maddie saga) belongs in jail.

    I’ve relaxed about writing this story, because it is obviously a sexual fantasy. I don’t think there are any schools, at least in developed countries, where headmasters get to strip their students naked and handle their bodies without supervision. So I can’t be seen to be defending some iniquity that actually exists.

    And I’m confident that no one could read this story and think, “Oh yes! Corporal punishment in schools was a really good idea. Let’s bring it back!” Or, in the case of several American States, “let’s keep it!”

    My story is pornography, as I understand the word, meaning that its principle literary aim is to give the reader reasons to come, while reading it. I think it’s pretty hot, and as a genre exercise it’s quite a good one.

    I’ve got another reservation, though. Though it’s not an objection to this story, but only to the idea that we shouldn’t try to do better than this story. That is, erotic writing is a genre, just like murder mysteries and science fiction. But everyone knows and acknowledges that murder mystery and science fiction novels and stories are often important literature, where the writing rises to a kind of poetry, and the vision of human behaviour is as revelatory and profound as anything in so-called mainstream literature.

    Critics usually say that those novels and stories have “transcended their genre”, which I think is a bullshit kind of praise, as if working in a genre stops you from writing and thinking well.

    I guess my issue is any idea that because it’s erotic writing it doesn’t need to be anything more than that. This Wicked Wednesday saga isn’t anything more than that: it’s just a hot fantasy, and I’m now enjoying writing it for what it is. But I’d hope to stay in this genre (because what’s more important and interesting than sex?), but to be writing about people, as revealed by their sex lives, because it’s such a rich field for writing.

    Critical respect for erotic writing may be a long time coming, but they’ll eventually catch up.

    Sorry if this is a confused and inconclusive response. My thinking on this is still confused and inconclusive, so that’s all I got.

    But thank you for your supportive comment!

  3. The strange thing with reading this is that it makes me feel uncomfortable, because I know what is happening here is not ethical, but since you haven’t mentioned her age, I am ‘okay’ with the story. I have read another story where someone mentioned that the girl was 14 and I just couldn’t get into the story because I kept on thinking that she’s only 14. This should not have bothered me, as by the time I was 14 I had been felt up by quite a couple of boys, but still it bothered me. I couldn’t properly explain why and had been accused of being a hypocrite. I’m still thinking about a reaction…

    That said, I do enjoy this story!

    Rebel xox

    • I did mention Maddie’s 18, so she would be able to choose whether or not to have sex in most jurisdictions around the world. The headmaster I haven’t described, or even given a name, because he’s seen only through Maddie’s eyes. But I think of him as being in his early 30s.

      That makes sense, I think, because Maddie can find him old enough to be attractively knowledgable in the ways of the world, while still being young enough to be fuckable. So if he wasn’t the headmaster of Maddie’s school, it’d be perfectly legal for them to meet and fuck.

      The ethical problem is that he’s supposed to be responsible for her education, and he needs to be objective; and that he’s got a position of authority over her which is going to influence her decisions.

      That said, it’s clear that within the ethics of this fictional world it’s consensual. Maddie loves what’s happening and enthusiastically wants more. And in Sexual Utopia, she should be allowed to have what she wants.

      In the world we live in, I don’t think people should change the rules to allow teacher/student sex to get any easier, though the policing of it in universities should probably relax a little. For various reasons for another discussion.

      What I think is a shame is the way our culture is panicking about same-generation sex, that is, between class-mates at high school, where people 13-18, say, are starting to explore and seek experience with each other. My attitude there is that that exploration is necessary and natural, and adults should just stay out of it as much as they can. Basically the adult role is to give information, especially on consent but also on pleasure. Intervention in specific cases should be reserved for where there are indications of harm.

      I don’t think two 14 year olds doing sexual stuff with each other is harmful. My oldest brother got caught having sex with a local girl when they were both 14. The two sets of parents discussed it, and decided that (beyond issuing and insisting on condoms from then on), the two kids involved were both good, fairly sensible kids, and so long as they did their homework, etc, and were discreet, there wasn’t really a problem. They stayed together for about 10 years, and are still friends. My previous girlfriend had consensual sex even younger, and remembers the guy with considerable affection. So early sexual experience is not necessarily tragic.

      I certainly don’t see any contradiction between having done sexual exploration younger than strictly legal, and being vehemently opposed to adults getting involved in that exploration.

      It comes down to power imbalance, mostly. Though I also think that any adult man who wants to fuck a 14year old girl is probably very immature, or a little too specific in his sexual tastes, and should be kept well away from 14 year old girls. For most men, I hope, just being on the train with them and listening to them talk is enough to make one desire very strongly not to have to engage with them.

      (I say that with respect for 14-year old girls, who are going through all sorts of shit. But ye cats, their interests are not my interests. I don’t care if Cody was staring at Charmaine’s tits in Science class, though the girls want the whole damn train to know.)

      But Maddie is 18, and would generally be considered to know her own mind. What’s happening in my story would be wrong in the real world not so much because of their respective ages, but because the older man has institutional power behind him.

      Anyway, it’s complex as hell!

      And I’m glad you’re enjoying the story!

  4. I have been enjoying this story too although yes there have been moments when I have felt uncomfortable about the Headmaster abusing his position but mainly I have read it assuming that what is being presented is not exactly what we think it is and that it is in fact adults role playing this situation.


  5. Yes. It’s more like a role-play involving adults, than anything real on our planet.

    I don’t think it’ll end with it being a role play, overtly, or “it was all a dream”.

    But it certainly isn’t real. And Maddie is telling this story to please and inform her lover, so it can be enjoyed but also taken with a grain or two of salt.

  6. Pingback: Wicked Wednesday: Maddie’s virginity (last hours 5) | Jerusalem Mortimer: Between the Lines

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