Ruler Spanking (With Pillow)

This is a real gentleman. He gives enough ruler spankings in his office that he keeps a pillow handy to support the faces of the big-chested ladies he bends over his desk:

ruler spanking over his desk

Artwork is by Bill Ward.

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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..."