Horse Whipped

Normally when you horsewhip someone, it means to strike them with a whip intended for a horse. But whipping them while they ride an already-painful wooden bondage horse also works:

horse-whipped on a wooden  horse anime manga hentai girl

It’s certainly working for her, judging by the trickle of natural lubrication she’s releasing…

(Full disclosure: Twelve years ago I posted a much tinier version of this same artwork, but in that one, it’s way harder to see that our sweet anime horse-rider is leaking evidence of her arousal.)

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Reform School Collective Punishment Movie:

Detention House 3: Delinquent Girls Spanked Amazingly Hard

before and after brutal caning photo
"...the girls are prepared in the reformatory’s punishment room, naked, lying on their backs on special benches, bound with their legs spread above their heads, shamefully showing the two holes usually hidden..."