Smack Her Again!

Debauchery in the classroom, comics are the bestest format for this sort of fantasy:

lesbian schoolgirl caning and sex

Click for a viewable size! Source unknown.

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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..."