Wicked Wednesday: Jennifer’s pleats and pleas 12: She’ll be coming when she comes

The previous episode is here.


Maddie was on her knees before me, skirt round her waist and her panties on the floor near the photocopier. She had her hands on my shoes, the taste of my come in her mouth, and a fresh, vertical cane stroke running down her left buttock. 

And she had a plan to tell me. She said, “You know Jennifer wants to give herself to you.”

“Let’s not get ahead of ourselves.”

“It’s silly to pretend you don’t know that. She wants you to take her under your wing. She wants to be disciplined, so long as it’s by you, and she wants you to steer her to achieve what she’s capable of. And she wants you to steer her sexually. Learn from you, but also give you pleasure.”

“You know this just by listening to her getting spanked?”

“I know where she is, sir. I was a girl like her, once. Come of age, but no idea what to do. I was doing a lot of acting out, sexually. But I wanted an adult man to teach me. Not schoolboys. So does she. She nearly came when she was over your knee. And she was giddy afterwards. Happy. Wanting you. God, the things that men don’t notice.”

I knew that Maddie was talking about herself at 18 as much as she was talking about Jennifer. Still, calling me obtuse, and her earlier use of the word ‘silly’, had pushed her over the line. I raised the cane and brought it down on her pale and round right cheek. “Ahhh!”

She wriggled and breathed through the pain, keeping her eyes on mine, the way she did when she sucked my cock. Because she was watching, I raised the cane again, and – when the alarm was clear in her eyes – slashed it down again, onto the reddening, slightly raised trail of the previous stroke.

Maddie waggled her delicious bottom harder, like a duck leaving the water, fighting to stay in her position while the pain ran through her. “Ahhh-Hooo! Oh, sir!” 

“Insolence, Maddie. Try to keep it to a minimum. Even when you’re telling me what you think I should do.”

“Thank you, sir. I’m sorry. I meant no disrespect, sir. First, I think you need to let her wait for a bit, and want you. She’ll give you a reason to punish her again soon. She’ll make sure of that. But let her wait till she’s feeling brave, and horny, again. It won’t be long.”

“All right.”

Who doesn’t enjoy aftercare?

“And when she does misbehave, you should punish her, certainly. Over your knee. Nice and slow. Let her enjoy herself. But this time you should let her come.”

“And then punish her for being a filthy girl?”

“You may, sir, but I hope you don’t. I hope you pretend not to notice, to spare her any embarrassment. But you should give her a lot of affection afterwards.”

“Rub her. Kiss her. Stroke her. Praise her?”

“Absolutely. A lot. She’ll need it. She’ll be dazed. It’ll be her first orgasm with a man. It should be happy.”

I thought about that. All advice is autobiography. Something bad had happened to Maddie in her transition from girl to woman. She was telling me to do what she thought would have been best for her. But I had no better map for how to lead Jennifer. I said, again, “All right.” 

Maddie kissed my cock, through my trousers. “And she’d love you to fuck her. and to teach her how to please you. Eventually you will. But in the meantime you should wait, and make her wait. Spank her, make her undress completely and bend over your desk naked for the cane: whatever you think she deserves. Then comfort her until she comes. But don’t take her yet. Let her make the move when she’s ready. She will.”

“Hmmm.” If Jennifer had come, there’d have been no stopping us. I’d have tipped her onto her back, on the floor of my office, and taken that virginity. That was why I’d had to stop so suddenly. On the other hand, Maddie’s approach seemed likely to introduce Jennifer to some of the wilder pleasures, while imposing frustration on me.

Maddie applied her tongue to where the tip of my cock was. “And then when you’ve shown her out the door you can take that nice hard cock of yours into the photocopier room. I’ll look after it.”

“Ah, I see. Motives. I’m sure you will.”

“May I suck your cock, sir?”


The next episode is here.

7 thoughts on “Wicked Wednesday: Jennifer’s pleats and pleas 12: She’ll be coming when she comes

  1. OMG this story really has me hooked… I find myself squirming in my seat, wanting to read on but also imagining myself either in Maddie’s or Jennifer’s place. Can’t wait for the next part!

    Rebel xox

    • Thank you for the nice words (and, I’m afraid, for the “squirming” image: squirming is one of my favourite things), and for undertaking Wicked Wednesday! Without that, this story wouldn’t exist!

    • Well, Maddie is fiction, alas.
      She’s partly based on a woman I knew, who, I think, liked the idea of me having sexual adventures so long as I told her about them. So she’d give me quite useful advice on seduction, in relation to specific women.

      She didn’t listen in from the next room and fuck me afterwards, though.

    • Thank you! I’m glad you like it!

      (It’s still a tricky one to write. I have to inhabit the skin of a much worse person than even I am, and steer away from the urge to humanise him. On the other hand, he and his equally wicked woman friend do make things happen.)

      And I think you’re right, that Maddie is generalising too much from her own life. But still, it may also be true that Jennifer may be more like Maddie, in some ways, than she thinks she is.

  2. Pingback: Prompt #240: New start - Wicked Wednesday & more

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