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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How It Started And How It's Going, The Movie:

Wild Party 2: Five Very Sorry Girls

before and after brutal caning photo
"...thirty vicious cane strokes for each delinquent young woman caught drinking on school grounds..."