In this admittedly over-the-top but to my eyes hilarious scene from the end of Prison Horror Story 4 by Predondo, one of the villainesses awakens in her own dungeon, strapped to a bench with her ass in the air and one of her former victims looming over her with a huge spanking paddle in hand, wearing a not-at-all small strap-on dildo. The former queen of the dungeon is a little bit slow on the uptake: “You’ll be sorry for this, bitch!” Oh, my. Somebody will be sorry and she might even be somebody bitchy, but it’s not going to be the bitchy person you think it is, Mistress:
Matters proceed very much as you might then expect.
Mistress, your stinging butt problems are going to get rather a lot worse before they begin to get even a little bit better:
From Dofantasy.
See Also:
This disciplinarian caregiver is from the cover of the book Bring Forth The Body. I’ve cleaned up the art a bit, but more could be done.
See Also:
I am not sufficiently certain that my knowledge of the fashions worn by ladies in decades past is so solid that I’m correct that the woman here having her bottom bared for a spanking is wearing riding attire, but I believe it to be so, and if I’m wrong, I’m sure somebody from the internet will come along to correct me:
Artwork is from the cover of a Jacula magazine.
See Also:
Not even breaking the paddle (which isn’t going to happen anyway) would save Cleo’s butt from this school paddling, because her principal has a spare paddle right there ready to hand. Nope, she’s in for it this time!
From Real Spankings.
See Also:
“SexySex” isn’t exactly a subtle pulp magazine title, but I guess it conveys the point well enough. And this lesbian whipping artwork comes from one of the covers of that magazine:

See Also:
The better sororities don’t allow tattoos, and they certainly don’t allow tramp stamps! Trashy beyond words, and definitely punishable:
From Clare Fonda Pass.
See Also: