Spanking The Waitress

They told her that waitressing in the fetish-themed bar would get her lots of good tips. What they neglected to mention is that she’d get tipped with spankings, not money:

waitress with inserted dildo and butt plug gets otk spanking in lieu of tips

From Slave Fair, a Dofantasy comic by Erenisch.

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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..."