Taught To Allow His Anal Explorations

She said something mean and rude when he gently intruded a slick finger in a place she wasn’t expecting. There followed a somewhat-lengthy four-way conversation between him, her, his paddle, and her bottom. She has received a lesson in politeness to her master, and a second lesson on the follies of promising “unlimited” submission when she didn’t mean it. She’s now ready to accommodate (politely! cheerfully!) a somewhat more intrusive exploration of her tight and innocent anus:

spanked until she is ready to allow her master to fuck her in the butt

Photo is from Assume The Position.

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A "Punished Delinquents In Tears" Movie:

Detention House 3: Spanked Inmates Made Very Sorry

blubbering blonde with a beaten ass
"...a heavy round wooden paddle with a hole in the middle that leaves fearsome red bruises. And then the shaking girls with beaten butts and tearful faces receive another terrible punishment..."