Sissymaid’s Warning

A sissymaid advises the newly imprisoned man:

Look – talking to you can cost me my hide. But let me warn you, they’re a mean bunch.

Kidnapped Male Slaves

Strange Lust

An attractive, appealing old F/m drawing with a bit of vintage sissyfication.

Strange Lust Femdom Feminization

Michael’s Petticoats

Sissy Lana’s depiction of a young man’s punishment for mocking a girl’s attire:

Go ahead Girls, peek under his skirts. You’ll see his naughty bottom is decorated in fussy frills.

So, Michael, are you truly sorry, and will you behave once your mother lets you get out of your petticoats? Will you make fun of my “prissy” dress and my “silly” gloves again? We’ll see!

Feminized Male Forced to Wear Petticoat Dress

Sissy Slave in Bondage

Uncomfortable bondage is the least that a man might suffer at the hands of these exceptionally sadistic women.

Male sissy slave in bondage

La Venus Negra

A ¡Historietas Perversas! – the black dominatrix seems to be exerting herself fiercely with the feminized man she’s punishing.

Black dominatrix feminizes man on his knees.

See also:

Helpless Sissy Slaves

Sissy slaves helpless in bondage.

The choice is yours You can have it relatively easy and submit to what we have in mind for you.
Everything OK Melanie?
Fine chief. Meek as a lamb after a week on punishment block.

Sissyboy Slave Helpless in Bondage

Sub Hubby in the Kitchen

Mistress Wife says:

It’s Mum. She’ll let herself in. I’ve invited her over to see the sweet little maid you’ve become.”

Sub hubby baking.

So you do wish you were a pie-baking sissymaid?

Sissyboy’s Purpose

Sissyboy in the hands of cruel women.

Now, you revolting little termite. I’m going to show you why you’re here.

Sissyboy Slave Cruel Mistress

His Pink Chiffon Dress

The Mistresses at The Agency make it clear to the man they’ve been tormenting that wearing the pink chiffon dress is not optional.

Come along now. This pink chiffon is really quite charming.
Stop struggling or I’ll have you hoisted up again! And leave you there! Ready on that button Sue?
Just say the word chief.

Male Slave Made to Wear Chiffon Dress

Feminization & Bondage

A modest portion of Paul Kamm’s femdom art featured elements of feminization.

Feminization Bondage

Punished in Petticoats

Mutrix Transvestism

I wonder: how many of you forced feminization fans actually dream of a maid feminizing you. Instead of your wife, girlfriend, co-worker of Angelia Jolie.

Then again who even thinks of the word petticoats here in the 21st century?

Punished in Petticoats Nutrix Sissy Fiction

My Brother’s Keeper

Mutrix Transvestism

My Brother’s Keeper says:

They made him a sex slave.

Cruel sister forces her young brother to dress like a girl.

Did you have fantasies of your sister forcing you to dress and act like a girl?

Teacher’s Pet

Mutrix Transvestism

Teacher’s Pet offers:

A sex-mad teacher transforms her prize pupil into a prissy transvestite …

Dominatrix Teacher Turns Boy into Sissy Transvestite

Sissy Slave Pet

Is this Chris of England?

Feminized Sissy Slave Pet Muzzled

Men in Skirts

For Feminization Completists

This is the sort of F/m artwork that irks me even when Stanton does it. This is a drawing of two women. It takes an act of almost insuperable will to see either of them as a crossdressing male.

Men in Skirts Transvestism Gene Bilbrew

Frédérique

Frédérique (Travesti). Histoire véridique d’un jeune homme changé en fille is another early 20th century sissyfication novel. Two illustrations by Pierre Bosser.

Frederique Sissyfication

Frederique Sissyfication Art French

Via BiblioCuriosa.

Sissy in Bondage

This feminization illustration reminds me superficially of comics artist Adam Hughes – who would be hugely popular if he ever did Femdom Art – but lacks Hughes’ skill.

Feminized sissymaid bound with chains

Siffyfied & Muzzled

Paul Kamm delineates one sure way of keeping a man silent: a muzzle.

Muzzled Slave Husband Sissy

Sissymaid Slave Labor

A sissymaid’s work is never done, at least not under the cruel control of Steffi:

Isn’t he sweet, Steffi? The poor guy will be tired. Nights in the laundry and after that drying our clothes. That reminds me, he has got to clean our pool. He’s got to get the scum out of the pool.

OK, we have a light in the garden, so he can work through the night.

Femdom sissymaid slave labor

Slave Training Begins

The Agency is a mid-1980s comic in which people are kidnapped and trained to be slaves and servants. The men are completely feminized.

A man finds himself in chains:

Him: What’s up with the whip you kinky bitch. Get me out of these cuffs!!
Her: Cur – I would suggest that you refrain from using such discourteous language.

Baz male slave training begins

The art is signed BAZ. I haven’t found out anything about him.