Michael’s Petticoats

February 21, 2013, 7:57 pm

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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!

Originally posted 2010-08-11 15:34:12.

Michael’s Petticoats
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Punished in Petticoats
2. Prissy
3. Piranhas in Petticoats

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Machine Turns Male into Female

February 24, 2013, 6:38 am

≫ Next: Sissy Husband’s Humiliation & Punishment

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A machine that would convert you from male into female would evidently satisfy many guys’ deepest cravings.

Machine Turns Male into Female
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Femdom Spanking Machine
2. Sissy Poking Machine
3. A Male Becomes Female

Sissy Husband’s Humiliation & Punishment

February 24, 2013, 4:39 pm

≫ Next: A Complete Guide to Petticoat Punishment

≪ Previous: Machine Turns Male into Female

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I don’t really care for F/m gender humiliation but I know the guys who like it hunger for the images desperately.

Originally posted 2010-12-26 14:52:31.

Sissy Husband’s Humiliation & Punishment
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Girdle Humiliation

A Complete Guide to Petticoat Punishment

February 25, 2013, 3:39 am

≫ Next: Girlfriend Feminizes Boyfriend

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A Complete Guide to Petticoat Punishment

Here it is in one handy volume. How to feminize and sissify your submissive male. Make him wear dresses, don wigs and use cosmetics. Everything a woman really wants to do to a man.

Elsewhere: petticoat discipline and forced feminization.

A Complete Guide to Petticoat Punishment
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Petticoat Bondage
2. Michael’s Petticoats
3. Mystery Package

Girlfriend Feminizes Boyfriend

February 27, 2013, 9:52 pm

≫ Next: Sissy’s New Catheter

≪ Previous: A Complete Guide to Petticoat Punishment

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Do you know who produced this feminization sequence?

Originally posted 2011-12-11 08:00:43.

Girlfriend Feminizes Boyfriend
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Girlfriend Punishes Boyfriend
2. Feminization Begins
3. They Made Him Love It

Sissy’s New Catheter

February 28, 2013, 2:01 am

≫ Next: Femme Males by Andy Kane

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Mistress:

Darling Nelson, this new pacifier / catheter will prevent your panties from being soiled when all my horny lady friends can’t resist handling you to completion. Also, you won’t need help undressing every time you need to urinate.

Sissy’s New Catheter
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Panty Sniffer
2. Domination in Full-Cut Panties
3. Scrubbing the Floor in Chains

Femme Males by Andy Kane

February 28, 2013, 2:06 am

≫ Next: Femdom Art of Satyn

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I especially like the first one. Certainly a SILF.

Femme Males by Andy Kane
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Femme Blanche
2. Chastised She-Males
3. Leashed Males

Femdom Art of Satyn

February 28, 2013, 2:50 am

≫ Next: Tranz: Forced Transvestism

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Femdom Art of Satyn
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

How do you feel?

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Tranz: Forced Transvestism

March 7, 2013, 8:02 pm

≫ Next: Dress Maker’s Dummy

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Another man being subjected to cruel enforced sissyfication (that he so deeply craves).

Does this sort of image give those of you who find the prospect of being feminized by a dominant woman pleasure?

Or am I wasting my time?

Originally posted 2011-02-21 07:21:16.

Tranz: Forced Transvestism
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. A Slave in Her Stocking
2. Mopping the Floor

Dress Maker’s Dummy

March 9, 2013, 4:38 pm

≫ Next: Fred’s Forced Feminization

≪ Previous: Tranz: Forced Transvestism

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Feminization art by Topfer (?).

Originally posted 2010-10-14 14:22:51.

Dress Maker’s Dummy
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. His Pink Chiffon Dress
2. Sissified Sub Hubby in a Yellow Dress
3. Her Dressmakers Dummy

Fred’s Forced Feminization

March 10, 2013, 5:53 pm

≫ Next: Making a Man Feminine

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French feminization novel Fred. Histoire véridique d’un garçon changé en fille was published by Select Bibliothèque in 1913. Artist identified as Tack.

Originally posted 2010-01-06 09:56:18.

Fred’s Forced Feminization
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. Ford: Forced Feminization & Enslavement
2. Ultimate Feminization
3. Tranz: Forced Transvestism

Making a Man Feminine

March 11, 2013, 3:59 am

≫ Next: Sissymaid Slave Labor

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Even The Bishop did some feminization / sissyfication art.

Originally posted 2009-10-26 08:59:58.

Making a Man Feminine
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. A Man is a Woman’s Pet
2. Vintage Sissyfication
3. Sissyfied (Mexican) Husband?

Sissymaid Slave Labor

March 11, 2013, 2:11 pm

≫ Next: Orgasm Denial & Bondage for the Sissymaid Slave Male

≪ Previous: Making a Man Feminine

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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.

Originally posted 2009-10-30 08:04:12.

Sissymaid Slave Labor
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. Steffi’s Kitchen Slave
2. Male Slave in a Cage
3. Femdom Wedding Night

Orgasm Denial & Bondage for the Sissymaid Slave Male

March 12, 2013, 12:06 pm

≫ Next: Juvenilization & Feminization

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Forced Feminization & Enforced Chastity

Advertising for a penis corset and chastity harness by Europa.

Orgasm Denial & Bondage for the Sissymaid Slave Male
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. Orgasm Schedule
2. Tranz: Forced Transvestism
3. Kneeling Male Sissymaid

Juvenilization & Feminization

March 15, 2013, 11:17 pm

≫ Next: TV Initiation Bondage

≪ Previous: Orgasm Denial & Bondage for the Sissymaid Slave Male

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This sissyfication drawing suggests juvenilization as much as feminization. The submissive sissy guys appears to be wearing a variant of the once infamous Little Lord Fauntleroy.

Artist unknown.

(Thanks to Sardax I now know the artist is Curtus.)

Originally posted 2010-11-22 11:46:34.

Juvenilization & Feminization
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Curtus
2. Lashing
3. Cruel Muse

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TV Initiation Bondage

March 17, 2013, 7:48 pm

≫ Next: Tame-Azons

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Gene Bilbrew art on a transvestism ‘zine.

Originally posted 2010-12-12 21:00:52.

TV Initiation Bondage
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. Denied
2. Femdom Christmas
3. Table Trample

Tame-Azons

March 20, 2013, 12:31 am

≫ Next: Please Sissify Me, Mistress … ?

≪ Previous: TV Initiation Bondage

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Tame-Azons was not the most felicitous term.

Originally posted 2011-05-17 10:03:01.

Tame-Azons
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

How do you feel?

Please Sissify Me, Mistress … ?

March 21, 2013, 9:03 am

≫ Next: Siffyfied & Muzzled

≪ Previous: Tame-Azons

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While sissyfication does nothing for me I get enough strange communications on some of my other sites to know how popular forced feminization is with some of you guys.

Then again, perhaps I’m frittering away my time useless and should stop posting the sissymaid sort of illustration.

Your call.

Originally posted 2010-01-15 14:01:09.

Please Sissify Me, Mistress … ?
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. Bondage Chair
2. Sadistic Call-Girl
3. Mistress & Her Lions

Siffyfied & Muzzled

March 24, 2013, 5:59 am

≫ Next: Hanging Mistress’ Laundry

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

Originally posted 2010-03-01 11:27:21.

Siffyfied & Muzzled
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

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1. Femdom Art of Paul Kamm
2. Her Human Male Pet
3. Kiss My Boots, Slave!

Hanging Mistress’ Laundry

March 25, 2013, 6:21 am

≫ Next: Girl Chasing Boy in Lingerie

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Semi-clothed-female-naked-male feminization.

Anybody have a men wearing aprons fetish?

Originally posted 2011-02-26 08:59:31.

Hanging Mistress’ Laundry
Femdom Artists - Illustrations of male submission, masochism & female dominance, sadism: paintings, drawings, sketches.

Similar Femdom Art:

1. Clovis Trouille’s Nuns
2. Weird Masked Women
3. Barbara O’Toole