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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Whipping A Blonde

We may have met this enthusiastic sadist before, but the welted blonde is new:

shackled blonde in tears getting a fierce dungeon whipping from a grinning black woman sadist

Whipping art is by Temon.

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Spanking His Personal Assistant

She knew when she took the job that he wanted her body and her submission more than he wanted her professional skills as a live-in personal assistant. That was fine with her! He was rich, not gross, and not excessively cruel. And the pay was excellent!

kneeling with a silver tray of spanking toys

Not cruel, did we say? Perhaps not. But some days, he’s more aggressive than others. These photos are from Master Lets Loose On Docile Servant from Kink Unlimited, and as the story goes:

Nicole Rey is a dutiful servant. When her master gets home from a long day at work, she pampers him like a well-trained geisha attending her emperor, helping him disrobe slowly and methodically, as if enacting some long-forgotten ceremony. Nicole knows to stay meek and humble before her master, bowing in front of him and presenting him with a selection of paddles and kinky toys to choose from…

On the days when her rich boss comes home full of stress, tension, and anger about weird shit that his hedge fund counterparties in Tokyo tried to pull, she always knows that she’s going get face-fucked and thoroughly reamed. But it’s actually pretty rare that he spanks her so thoroughly first:

spanked servant

spanked executive assistant

punished submissive

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