Anal Under The Crop

There are a few things that a good girl may be reluctant to do, especially if she’s shy and had a conservative upbringing. But a few brisk whacks with a riding crop can create a powerful incentive!

after he spanks her pussy several times with his riding crop, he slowly works his cock up her ass while she reluctantly submits to his anal sex ambitions

Photo is from Maria Bellucci Submits, which is a Sex And Submission shoot at Kink.com from back in 2008.

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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..."