Don’t you just love the look on her face as she goes inward to process the pain of that big honkin’ leather strap?
Pic is from Real Spankings.
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Dirty sock in her mouth or not, she certainly seems to be making the most of this erotic spanking with his belt:
From a sex comic called Kristy’s Cafe by Tulli and Morucci.
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Abel has found a newspaper account of sorta-consensual (as in, agreed-to to avoid prosecution) private birchings for “female shoplifters of gentle birth”:

I doubt that the original “London Truth” source is any more reliable than Правда ever was, but it’s a fun tale nonetheless — the sort of tale that gets recounted in the funny papers because it’s slightly lurid and because enough people sort of want to believe it even if they actually don’t.
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The best part of Her First Punishment has always been, in my view, the authentically-unhappy faces of the harshly punished girls. This pair of faces is no exception:

It took some sleuthing, but I tracked these pictures down a bit further, and learned that the footage from which these faces were captured is also available on Russian Slaves #41.
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I found this vintage French-looking spanking illustration on WaldoBlog:

Waldo makes the signature out as T d’ Y (which would be “T from Y” or “T of Y” I guess) but that doesn’t tell him (or me) very much. Anybody familiar with the artist?
Waldo has this to say (after a little mucking about with Google Translate) about the scene:
[It] shows a young girl whipped on a park bench by a woman in severe pellerine. The poor girl has her wrists bound behind her back and does not wear panties. This punishment, was it planned? Best of all, the guardian of the square, rather than intervene, plays voyeur!
“Pellerine” there is a word that baffled Google Translate and me, alike.
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I’m not sure what vintage porn star Ebony Ayes did to find herself ass up over a couch with her sporty shorts pulled down (and later, completely gone), but I’m guessing she must have let her inter-woman status games go too far, until her man got annoyed. There’s only so much of that plastic-talon “Look, girls, I’ve got longer faker nails than you, I’ve clearly got a richer sugar daddy than you do because obviously I couldn’t do a lick of work with these things and unlike you working-class sluts, I don’t have to” posturing a fellow can take (and pay for). Amirite?
You gentlemen of the caning persuasion may also find subtle inspiration in the lovely lattice of shadows across her bottom that appear to have been cast by the Venetian blinds…
Pics are from The Classic Porn, and sadly, there’s no actual spanking to be seen.
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