Let’s Tie Up Canada, She’s Pretty

I haven’t bothered to research the detailed context of this old political cartoon, but the gist is pretty obvious. And Canada is cute, all wrapped up in rope!

bondage political cartoon of uncle sam buying a tied up canada for a sack of gold

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Angry Blonde On Her Knees

Siri, what is best in life? Oh, you say it’s an angry blonde, cuffed at wrists and ankles, forced to kneel and await my pleasure on my extremely secluded back deck? I can’t argue with that!

angry cuffed blonde

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Cold Backyard Slave

If you live far enough north, just making your slave stand hooded in your back yard becomes a pretty cruel punishment:

naked slave in the snow wearing nothing but a rope harness and a gunny sack burlap bag hood

Photo is an old one from Insex.

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Collared Deep Throat Challenge

His cock is massive. It’s going to be a real deep-throat challenge. But the shiny chrome-steel collar argues that this woman is going to have to find a way…

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Chained To The Marital Bed

You wouldn’t think an eager new bride would need to be chained to the headboard of the brass bed, but maybe she tried to play the old “not on the honeymoon, dear, I need time to adjust to the idea of sex” routine on him and he was not having any:

newly married wife is chained to her own brass bed

Notice how the brass is dark and tarnished everywhere except where the chains go, which is bright and shiny as if from frequent use as a bondage attachment. Perhaps his new bride simply didn’t realize that the perv she married had very specific notions of what a fun evening of sex should look like!

Artwork is from the cover of Bride For Bondage (Bondage House 1979, BH8064).

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Tasered, Tied, and Ass-Tapped

This woman has had a rough day. How many sets of stun gun marks can you spot on her body? And now the loss of her anal virginity is being streamed live for the world to see:

chained to a desk for bondage anal and stun gun torment

Artist is Harris Hero.

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Ten Chastity Belt Cartoons

The July 1963 issue of Hi Life, a men’s magazine that sold for fifty cents, included a “Men’s Humor” feature by cartoonist Don Oreheck. Titled The Keys To The Kingdom, the feature included ten different cartoon gags about chastity belts. As the editors introduced them:

In days of old, the knights were bold… in more ways than one. While some knights were off waging war in the Holy Land, the rest were home, storming other bastions. As a matter of fact, for all parties concerned, the very success or failure of the Crusades depended on a tiny key… and the treasures it did, or did not, guard. Here, Cartoonist Don Orehek presents his version of the real battle of the Crusades… the battle for the Keys to the Kingdom.

key swallower

rat trapped chastity belt

a good locksmith

spare keys for the wenches

chastity belt with combination lock

lotsa kids and a broken chastity belt

expanding chastity belt for a growing woman

stuck in his armor

found the spare keys to the chastity belt

her husband is back, stop fooling with the chastity belt

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