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Sissy at the Beach

Sissy puts lotions on Mistress’ back at the beach. Sissy at the Beach Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches. Similar...

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Sissy’s Penis is Joke

Everybody knows that sissy has a hilariously tiny cock. Sissy’s Penis is Joke Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches....

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Sissy Kidnaped by Space Mistress

Even in the far future in outer space sissies will still suffer humiliation and degradation. Sissy Kidnaped by Space Mistress Femdom Artists - Illustrations of male submission, masochism & female...

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Supergirl Sissy

Which super-heroine do you think is the best for sissies? Supergirl Sissy Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches....

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Sissy on Mistress’ Leash

And Mistress’ strap-on dildo. Sissy on Mistress’ Leash Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches. Similar Femdom Art:...

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Only Women Should Vote

For female superiority / female led relationships fans. Only Women Should Vote Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings,...

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Donkey-boy is Pathetic

Donkey-boy is a wimp who runs errands for the women who mock him. Donkey-boy is Pathetic Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings,...

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Sissy Librarian’s Embarrassment

Sissymale librarian’s humiliation. Sissy Librarian’s Embarrassment Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches. Similar...

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Sissymale’s Clean Penis

It is indeed very important to keep its worthless genitals clean at all times. Sissymale’s Clean Penis Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism:...

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How Bob Became Barbi

Little did the young man the fate the two seemingly friendly young women had planned for him. How Bob Became Barbi Femdom Artists - Illustrations of male submission, masochism & female dominance,...

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Sissymale in the Milking Dungeon

Sissy slave stays chained and milked. Free for small periods to eat and allowed a minimal amount of sleep. Sissy lives to be drained of ejaculate. Sissymale in the Milking Dungeon Femdom Artists -...

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Sissymale’s Torment & Training

I think this sissy slave is being given some sort of specialized training but can’t guess to what purpose. Sissymale’s Torment & Training Femdom Artists - Illustrations of male submission,...

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Sissy’s Pathetic & Small Penis

Sometimes Mistress is in a cranky, crabby mood. Nothing lightens her bad mood than a spell of bondage in the bondage with one of her sissy slaves. She relaxes by poking this sissy in the genitals,...

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Girl Chasing Boy in Lingerie

Li’l Abner wasn’t a crossdresser. He donned drag to hide from the woman chasing him. She’s his future wife Daisy Mae and it is Sadie Hawkins Day, a holiday in Dogpatch USA when women can force the men...

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Adult Baby Sissy’s Full Diapers

How embarrassing for the sissy. How disgusting for the Mistress. How does she deal with this. What are the consequences for sissy? Adult Baby Sissy’s Full Diapers Femdom Artists - Illustrations of male...

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Sissy’s Public Wedding Humiliation

The women enjoyed plotting the distress of two men. The public humiliation of the exposed sissy male. And the groom’s degraded shock to learn that the women had tricked him into marrying a man. A trap....

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Sissy Servant Storage Problem

Storing your sissymale servant when not in use doesn’t have to be a problem. The sissy exist for your please. It is an object and merits no compassion. A cheap rope is all a Mistress needs to bind the...

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Degraded Sissy Cuckold

Mistress Wife is so inventive in the ways she degrades her cuckolded sissy husband. Here she allows the poor creature to lick the soles of her feet while she enjoys tim with the real man in her life....

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Sissy “Beauty” Pageant Winners

Women mock and deride pathetic sissies who think winning a sissy pageant earns them anything more than a booby prize. Sissy “Beauty” Pageant Winners Femdom Artists - Illustrations of male submission,...

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Sissy Male’s Self Discovery

Was this how it was for you? That first miraculous moment when you saw yourself in women’s clothing? The quick surge of intense arousal. The discovery of a fundamental truth that would shape the rest...

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