Wicked Wednesday: Cry if I want her to

Jennifer stood there in my office, little tartan skirt lifted at the back, panties down to her mid-thighs, waiting for Maddie to smack her with the ruler. She’d agreed she deserved this encounter with the ruler, and now there was only the agony of anticipation.

I said, “Good girl. You’re right; you do deserve it. Now, today’s going to be a little different from our earlier sessions, Jennifer. The first difference is that you’re going to count, today. You can treat this little ruler-spanking as a practice. After each smack, you’ll count it out loud, and then you’ll say thank you, to Maddie, and to me. Understood?”

Jennifer had her arms round my neck as I held her still. She looked into my eyes. Something in this situation was making her smile. “Yes, sir. I count, and I say thank you, to both of you.”

“Good girl. That’s a good girl who wants to learn.” Jennifer beamed, a very happy girl, about to be spanked. “Now, you make sure you count out loud as I’ve told you.”

“Oh yes, sir.”

“Maddie, not too hard, for these. Just make sure she feels them. Go.”

A second later there was the characteristic SNAP of wood on flesh, and Jennifer jolted in my arms. She pressed against my cock, and felt the involuntary movement I made in response: a pelvic thrust, for Jennifer. She held me tighter, and lowered her head to rest against my chest.

“Oh, sirrrr:” it was almost a purr. Then she remembered and said, “One! Thank you, Maddie! Thank you, sir!” A moment later, after a few seconds’ thought, she said, “May I have another?”

“Maddie, oblige the girl.” Maddie did, and the girl jolted again, in my arms, pressed against my fully erect cock.

“Two! Thank you, Maddie! Thank you, sir! May I have another?”

I had to laugh at Jennifer’s earnestness, in times of physical punishment. She was such a sweet girl. “A little harder, I think, Maddie.”

Maddie said, “I have to agree.” The third smack was possibly twice as loud, and this time Jennifer had to breath a few times, before she could count and thank. She had the sense not to ask for another.

I said, “Good girls. Both of you.” Jennifer, who was nobody’s fool, shot a look at Maddie. Maddie was a good girl too?

“All right, Jennifer. I told you today is going to be a little different. Take your clothes off, and hang them up, please.”

She glanced at Maddie, and looked at me. “Sir? Everything?” She hadn’t been naked in front of me before. 

“Do as you’re told, Jennifer. Maddie will help you, if you need it. But if you take too long about it, Maddie can show you that that ruler isn’t always a toy.”

She blushed. “Um.” She turned to face the wall, and took her blazer off. She unbuttoned her shirt, and took it off, revealing her bra strap, crossing a pale, slender back. She reached for the catch.

“No, Jennifer. Skirt next.”

“Yes, sir.” She unclasped and unbuttoned the skirt, and hung it up. Then she took her shoes and socks off, putting her socks inside the shoes and placing them neatly on the floor under the rack.

Then she turned to face me, in her bra and panties, arms still protecting her modesty. That, of course, would not last.

Jennifer was beautiful, with just a little puppy fat at the tops of her thighs, a very appealing dome to her tummy, and her breasts just a little fuller than I’d expected. She looked every inch a girl who was about to get the slipper. She was very aware of her situation: this was her party, and she’d cry if I wanted her to. 



3 thoughts on “Wicked Wednesday: Cry if I want her to

  1. What a vision!

    This song has popped into my head in scene before, causing laughter on my part and intense crossness for my sadistic friend. But, it was his party and I’d cry if he wanted me to.

    Thank you for your post, and reminding me of a great night.

Leave a Reply

Your email address will not be published. Required fields are marked *