Chicago Feminization

Chicago Sissy Training

Chicago Feminization - Photo Gallery



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These photos are male friends of mine who enjoy dressing en femme.  Some of them also like bondage, spanking, role-play, humiliation, outings, and so forth. Keep in mind that your session will reflect your needs and desires. These photos do not necessarily represent what you'll choose to do during your session. It is entirely up to you to set your personal limits and discuss your interests with me.


"Your ability to read things in people, that they don't even realize, is phenomenal."

(a quote from an e-mail from Belinda, a favorite client, the one in the Edwardian sissy maid costume)


Sissy Baby Jessica Shows Off Her Dress   Sissy Baby Jessica Shows Off Her Dress   Sissy Baby Jessica Shows Off Her Dress


Sissy Baby Jessica Shows Off Her Diaper   Sissy Baby Jessica Shows Off Her Ruffle Butt


Sissy Maid Jessica Chicago   Sissy Maid Jessica Chicago   Sissy Maid Jessica Chicago


Rebecca Crossdresser Chicago   Rebecca looks sickening!   Rebecca's flawless makeup - done by Goddess Madeline


MTF Transformation - Rebecca   Rebecca Corset Heels   Femme Transformation   Hogtied Sissy


Hog-Tied Sissy   Bitch Bobbi hooded!   Bitch Bobbi hooded, bound, and thigh-highed!   Bitch Bobbi hooded, bound, and cock-ringed!


Bitch Bobbi hooded, bound, and cock-ringed!   Ask to look like a whore, and it's gonna happen!   Notice the locking heels?   Cheap makeup and lots of it!


Chicago Crossdresser Martina   Chicago Transvestite Martina   Chicago Sissy Slut Martina


I use fresh makeup brushes on every client!   Forever 21 haul for the Sissyville Salon wardrobe.


A very small sampling of Sissyville Salon's sissy shoe collection.   Let's make your nails look fierce!


CB-2000 Chastity Device Chicago   CB-3000 Chastity Device Chicago


CB-6000 Male Chastity Device Chicago   The Curve Male Chastity Device Chicago   ExoBelt Male Chastity Device Chicago


Sissy Baby Chicago   Chicago Sissy Baby Mistress   Sissy Baby Chicago   Sissy Babies Chicago


Chicago Dominatrix for Sissy Babies   Chicago Sissy Baby Mommy   Sissy Baby Benita bends over to expose her plastic pants and diaper!


Bobbi's dickie is pumped up and his scrotum is stretched with stainless steel rings!   A Peenie Petal always flatters a sissy stick!   Rubber Doll


Rubberdoll   Electro Urethral Sound and Scrotum Clamps and Stainless Steel Cock and Ball Rings   Electro Urethral Sound and Scrotum Clamps and Stainless Steel Cock and Ball Rings   Electro Urethral Sound and Scrotum Clamps and Stainless Steel Cock and Ball Rings


Chicago Sissy Training   Chicago Sissy Slut Training   Chicago Sissy Maid Training   Chicago Diaper Sissy


Chicago Sissy Baby Girl   Chicago Sissy Baby   Sissy Maid Michelle must be on her period!


Sissy Maid Michelle is poking out of her pink panties!   Sissy Maid Michelle is pretty in pink!   Sissy Maid Michelle has on a frilly pink petticoat!   Pretty bitch - look at her ass!   Pretty bitch - just look at her!


Pretty bitch has a pretty sissy stick!   Pretty bitch has a very pretty sissy stick!   Sissy Laura all dolled-up   Helen at Be All   My personal secretary bending over! What does she want?


Ready For Forced Gyno Exam   Bound & Gagged For Forced Gyno Exam


A shaved cunt is an absolute must!   A fishnet bodystocking and Latex thigh high boots!  What do you suppose she's in for?


She's in for a breast enhancement!   Those C cups are sweet!   Sissy Maid Marsha - one never forgets her first sissy maid!


Edwardian Sissy Maid Belinda   Edwardian Sissy Maid Belinda - at your service!   Ms Belinda ready to step out!


Ms Belinda asks - where are we going, Goddess?   An elegant and charming lady - Belinda!   Belinda has a beautiful smile!


Belinda looks sweet in her glasses!   Belinda posing nude!   Sissy Maid Belinda!   Sissy Maid Belinda!


Sissy Maid Belinda!   Sissy Maid Belinda!   Sissy Maid Belinda!   Sissy Maid Belinda!


Sissy Maid Belinda!   Latex bondage for a naughty sissy!   You can't go wrong with a blue wig and a farmer's tan!   Sissy Chrissy


Sissy Chrissy   Sissy Chrissy


Sissy Baby in Chicago   Sissy Baby Jessica   Sissy Baby Jessica in Chicago   Sissy Baby Jessica spanked in Chicago


Sissy Jessica Wears A Peenie Petal   Sissy Jessica In My FemSkin, Blindfolded, & In Bondage   Sissy Jessica FemSkin   Sissy Jessica in a FemSkin!   Sissy Jessica - FemSkin - Vibrator - 'nuf said?


Sissy Jessica as a beautiful ballerinal!   Sissy Jessica in bondage!   Sissy Jessica bound and forced!   Now, that's a tuck job!


Marilyn the classy secretary   Marilyn stepping out in a see-thru outfit   Secretary Marilyn in a summer dress!   Secretary Marilyn bound!   Secretary Marilyn in bondage!


Secretary Marilyn corseted and helpless!  That's a butt plug harness and a spanked ass!   Sissy cross-dresser in rope bondage!   Sissy cross-dresser in the pillory!   Sissy cross-dresser in rope bondage!


Sissy crossdresser cheesecake!   Cheesecake on a spanking bench!   Helpless sissy!


Sissy crossdresser in a bondage chair!   Tied and humiliated!   Bound and gagged!


Tig old bitties!   Sissy Maria in a strait jacket!


Sissy Maria bound and helpless!   Sissy Maria tied with scarves!


By Madeline Schadenfreude


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