Redden Her Bottom Before Sex

Right here we have a gentlemen who clearly understands the proper use of a leather strap as foreplay:

girl with a flaming red bottom is fucked from behind by a man holding a large leather strap with holes in it

Artist is Tumtumisu.

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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..."