Claire said, “Sir? I’m sorry, I’m not a schoolgirl any more, and I’m out of practice with the cane. This is hard for me. Can I hug you, sir? Please. I want to continue till I’m properly punished. But I just need … I need you to hold me for a moment, sir.”
I considered the request. My instinct was to say no. Discipline came first, and should be strict. On the other hand, Claire was an adult woman, and hadn’t felt the cane in years. I said, “Maddie, help Claire up.”
When Claire rose to her feet Maddie turned her, and pushed her in my direction.
I caught her, and held her tight. She put her arms around me and her knees seemed to sag; she was relying on my to hold her upright. I held her tight against me, then, when she was back on her feet I ran my hands down her back, then gently clasped and rubbed the skin of her fresh-caned bottom. She shivered, and then relaxed against me again. Skin contact is so beautiful.
She said, “Oh fuck, sir. I know I need this, I mean the cane. But it’s so hard.”
I said, “Shhh, Claire. You’re doing well. And you’re being a brave girl. Brave as any schoolgirl.” She smiled, but the pain was still building for her. I had a thought. She needed to think of her ass in an explicitly sexual context. At least, and at worst, it could be a distraction from the cane. “Tell me, Claire. Your husband. Or his friend. Did they fuck you up your ass?”
“Maddie’s right: that’s insane. They were both out of their minds. You have a gloriously pretty, sexy, fuckable ass.”
Claire was still puzzled, but she said, “Thank you. Sir.”
“Well, has anyone had your ass. His cock in you?”
“Not since high school. I sometimes let boys … You know. Instead of getting me pregnant.”
She seemed to look inside herself, while she considered. “It was okay. No, sometimes it felt perfect: just right. You know, not most of the time. They were just boys. But sometimes it just reached into me. Still, once I’d had vaginal, I, um, never looked back.”
“The buttplug. Medium one. Get it out and lube it, please.”
Maddie said, “Sir!”