This one's 499 words, and, as customary, is copyrighted to me, Andrew Angerclashes, as per 2009.

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When dinner was almost over he played his hand.

He pulled his briefcase out from under the table, releasing the clasps. It popped open and her eyes followed suite.  Inside was a paddle! It looked uncannily like the one that was used on her back at school.

She seemed to shrink. She was a succesful lawyer, but looking at the paddle she felt fifteen again. Her belly tightened and she trembled. "What is this for?" she asked, unable to keep a tremor out of her voice.

"To bring back memories, sweetie. Do you remember when it was last used on you?"

Her logical mind pointed out that he could not know that it was used on her at all. But instead she said, "Eleven years ago."

"Do you remember the punishment?"

"Vividly."

"I'll bet you do. Twelve pops for wearing a skirt that was certainly not part of school regulations, correct?"

"How did you know that?" Her poker face didn't seem to be working today!

In response to this, he began quoting. "Name: Tarah Thompson. Date: 5th May, 1998. Infraction: Dress code violation. Disciplinary action: Twelve with paddle. Comment: Tarah was warned about her skirt length."

He grinned - she was blushing. "Isn't that about right?"

"So that's what you're all about? Some random creep who looked at the school records?"

"Ok, how about I tell you something about yourself that's not in the records? That paddling was the most painful one in your life, but you wanted it. You found an easy rule to break and exploited it to get your rear end warmed. You were one of their best students. But your name shows up in the school's disciplinary board register too often!"

"No!"

"Afraid so, sweetie. You're into this."

"No. You're wrong. I make more per year than that shitty old school does, probably, and I have no time for schoolgirl games."

"Let's employ an acid test, then, shall we? I want to spank you like a naughty schoolgirl. I want to bend you over my knee and slap your bottom until you're howling with pain, and then I want to bend you over my bed and paddle you as a finale. Most women assuredly do not want that. Any one of those would get up, tell me to fuck myself, and storm out. But you are intrigued. You will not allow yourself to escape. Your cue."

She stood up. "Go fuck yourself." People turned to stare. She stormed out.

Oh well, he thought. I played it too aggressively. He paid and left.

As he was fishing out his car keys, he saw her. Apprehensive. But determined. "You're some kind of pervert, aren't you?" Her tone was not accusatory.

"Nope. We can talk on the way." He took her arm.

As he helped her into his car and started the engine, he remarked "Oh, that stunt in the restaurant ensures that you receive comeuppance with lowered panties."

She blushed, now committed to her evening of pain.