She Would Enjoy His Stick

The double entendre makes this gag; when the cop says “You’re getting off easy tonight, I should use my stick!” his billy club is not the first thing that rises in anybody’s mind’s eye!

cop spanks woman with his hand and threatens something more

Was that too risque for some magazine editors in the ’50s and ’60s? Perhaps so; Chicago Spanking Review has various versions with at least one different caption. A very similar cartoon drawn by Bill Wenzel actually has the cop, rather implausibly, using his stick for the spanking:

cop spanks woman on park bench cartoon

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Cane Training The Royal Maids

I don’t normally post art that’s visibly constructed on a foundation of photoshopped collage work, but I’m making an exception here for King’s Maids School by Danilo, which is part of his Servants And Maids collection:

weekly punishment of the royal maids who have screwed up in their duties

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His Cruel Caning Orgasm

It’s lucky for our unfortunate bondage caning victim that her tormentor has a bit of a premature ejaculation problem. Because quite clearly, he never intended to stop caning her before his over-excited cock spurted all over her bottom and the cruel welts he put there:

cruel bondage caning until the man with the cane shoots his jizz all over the punished girl

I don’t recognize the spanking artist. If you do, please tell me in the comments!

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“Hold Still… Or Else!”

This is a humiliating punishment exposure, but he’s making it very clear to the young lady: if she moves, her spanking will be much worse!

diaper position punishment spanking

Photo is from Peter Birch.

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Judicial Caning In The Punishment Stocks

I can’t identify the uniforms in this severe caning scene, but I imagine it’s a judicial punishment in progress. The spanking bench conveniently outfitted with wooden pillory-style restraints speaks to me of an institution that dishes out quite a lot of this sort of discipline:

helga bode judicial caning in the spanking stocks

Artwork is by Helga Bode.

Update: the Spanking Art wiki has a smaller version with an original caption in German that seems to confirm this punishment is taking place at a police station:

at the police station punishment

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Blowjob Whip Training

When he offered to give her blowjob training, she was intrigued. She had no idea at all that he was going to handcuff her and use a whip, but she did have the foresight to put a hidden camera in her bedroom. She had a feeling it would be a hot session that she’d want in her video library:

whipped, handcuffed, and forced to suck

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Lesbian Spanking Party In The Shower Room

Communal showers, wet angry lesbian bullies, a ping-pong paddle: this is a recipe for somebody getting a red sore bottom!

held down and spanked by three wet angry lesbians

Artwork is by NaughtyGirls.

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