Maddie went to the cupboard and took out the buttplug, annointing it thoroughly with lube. I mouthed, “Good girl,” at Maddie, and then kissed Claire. “Claire, I don’t think you have the right to choose, on this. I’m going to fuck your ass while I’m fucking you this afternoon. Just say, ‘Yes, sir,’ because I’m not asking you for permission. I’m just letting you know.”

“Um.”  Claire looked at me warily. But there was a kind of smile on her face. “Yes, sir, then.”

“Good girl. And right now, while I’m punishing you, you’ll do what I think is best for you. I think the buttplug will give you something to focus on that isn’t pain. That’ll make it a little easier for you. So you say, ‘Thank you for putting a buttplug up my ass while you’re caning my bottom, sir.’”

Claire said, “I asked you to cane me. This is more … Still, I don’t think you’re wrong. I must be crazy. I mean, ‘thank you for putting a buttplug up my ass while you’re caning me, sir.’”

I patted her poor, caned bottom. “Good girl, Claire.” I put my hand in her hair, behind her left ear, and kissed her. She kissed me back. She closed her eyes. Then I smacked her bottom and she squealed sweetly. “Now go back and assume the position. Same as before. Keep your butt up for me, Claire.”

Claire lay her body down on my desk, holding tight, her bottom up and poised. “Like this, sir?”

She knew how desirable she looked. I took out my phone and took several pictures of her ass, so she could admire her marks later. I said, “Very much like that, Claire. Maddie, do your thing.”

Maddie stepped behind Claire, and patted her bottom fondly.

She said, “Keep still, Claire”, and pushed the buttplug against Claire’s tight little entrance. Her rectum suddenly gave, and Claire squealed as the plus entered her, half alarmed and half submissively aroused.

Maddie pushed firmly, letting the thickest part of the plug enter Claire’s anal tube, until her muscle closed again on the thinner part of the plug.

She gave Claire a sharp smack across her welted skin, and said, “There. Good girl, Claire.” A red jewel peeked at us, from the circle that stayed outside her anal opening.