Chicago Feminization

Chicago Feminization Photo Gallery


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The Subjects

These photos are male friends of mine who enjoy dressing en femme. Some of them also like bondage, spanking, role play, humiliation, outings, and other kinks. Keep in mind that your session will reflect your needs and desires. At my feminization studio you help build your own custom session. You tell me your needs and desires, then I create a perfect bespoke experience for you based on that information.

The Midwest's Finest Feminization Studio

I carefully curated the best collection of crossdressing, feminizing, and sissifying items money can buy, then I created the foremost gender play studio in the Midwest and the entire United States. I spent two decades and well over $100,000 building a facility that meets every need. I challenge anyone to even come close to the complexity, detail, and sheer wonder of my space. I have everything. Sissyville is my magnum opus.

Under Construction

Sissyville Transformation Room

Displayed in Sissyville are more than 100 unique wigs, including front lace, full lace, human hair, monofilament, short, long, and mid-length. Every color of hair is available from blonde to red to rainbow. I will choose the perfect wig for you, then apply it using a few tricks I have up my sleeve.

The makeup director's chair is where I perform my magic, taking men from drab to fab. Sissyville has an airbrush system and disposable makeup applicators, so there is never a chance of contamination. Everything is done under the strictest aseptic protocols. There are hundreds of shades of lipstick, lipliner, lip balm, and lip gloss. I will give you the perfect pout. You will look fantastic batting the long false eyelashes I apply. Numerous eyeshadow palettes, countless eyeliners, and innumerable mascaras will make your peepers look very feminine. I have dozens of shades of foundation and concealer to cover facial hair and even out your complexion. I will complete your look by using contour, blush, and highlighter to sculpt your face from masculine to feminine. A bit of powder, then a spritz of setting spray, and your look is complete. Drag queens taught me every facial feminization makeup trick I know. You will look stunning.

Now that your hair and makeup is done, it is time to sculpt your body into a feminine hourglass silhouette with a gaff tucking panty or V-panty, butt and hip padded undies, a see-thru pocket bra to show off your luscious new nipples, breast forms, or breastplate, and a waist cincher or corset.

Once your ladylike figure is achieved, I will pick appropriate shoes or boots for you to wear. Sissyville has hundreds of pairs of footwear in ladies sizes 7 to 18.

Every clothing item in Sissyville is sized to accommodate any physique, from xx-small to 8x.

Sissyville has breast forms and breastplates from a modest A cup to comically huge.

My arsenal for hair removal, should it be a request, includes surgical clippers with disposable blades, disposable ladies razors, ladies shaving lotion, tweezers, wax, and depilatory cream.

At this point, I shall choose your attire. There are over 100 pairs of brand new panties in every color, style, and fabric imaginable. You get to keep any used during your session. Take them home and enjoy them, if you want. Will I pick layers of petticoats, ruffle butt white tights, and a pink satin sissy maid dress? Perhaps, I'll choose a trashy leather mini skirt, fishnet stockings, and a cheap-looking tube top. How about a role play outfit, such as bride, cheerleader, schoolgirl, Goth girl, or secretary? Maybe, you will wear a pretty sundress or formal evening gown. A classic choice is a tight black pencil skirt, white silk blouse, and black seamed stockings.

After you are dressed, it is time for accessories. Sissyville's jewelry organizers contain rings up to size 14, as well as adjustable models. Add to that countless stretch bracelets, necklaces, clip-on earrings, pierced earrings, tiaras, belts, handbags, outerwear, scarves, and the list goes on.

Before your visit, when we negotiate your session, your role, limits, preferences, must-haves, allergies, health, and so forth will be discussed and taken into consideration.

You may choose to be a sissy baby, sissy slut, sissy maid, hapless kidnap victim who is forced feminized and distraught after being forced into prostitution, mindless bimbo fembot programmed to service both males and females, beta male coerced into life as a cuckold wimp, hypnotized subject, panty thief, prey to a femme fatale, loser employee forced to crossdress to amuse his boss or else lose his job, and the list goes on, limited only by our imaginations. Quite possibly, you are simply a crossdresser seeking advice or a makeover. You might be naughty and need domestic discipline. There is a chance you are kinky and wish to segue into a dungeon or medfet scene. Another option is a public outing to a drag show, restaurant, nightclub, bar, movie, or other venue. The possibilities are endless.

Transformation Studio   Transvestite Wigs   Transformation Studio Shoe Racks

Nail Polish Wall   Sissy Wigs

Ladies Room

The ladies room is directly off Sissyville. You are invited to shower before your session, after, or both. The ladies room is immaculately clean. It is stocked with high-end body wash, soap, shampoo, conditioner, mouthwash, makeup remover, and spray deodorant. Fresh, clean towels are provided.

Sissyville Ladies Room   Sissyville Ladies Room   Sissyville Ladies Room

Sissyville Ladies Room  

Sissy Baby Nursery

Quite simply, I have the finest sissy baby nursery in the world. In fact, I don't think another exists. All the ABDL nurseries I have seen are either dedicated to adult baby boys or they blend adult baby boys and sissy babies in the same space. That is not good enough. You deserve the best. Having to look at a toy truck, while you are trying to get into sissy baby headspace is disconcerting. Lots of little girls play with trucks, but sissy babies are ultra-feminine. They need a puffy pink bubble that cannot be penetrated by masculine thoughts.

Sissy Baby Nursery   Sissy Baby Nursery   Sissy Baby Nursery

Nursery Bathroom

The nursery bathroom is next to the sissy baby nursery. You are invited to shower before your session, after, or both. The nursery bathroom is immaculately clean. It is stocked with high-end body wash, soap, shampoo, conditioner, mouthwash, and spray deodorant. Fresh, clean towels are provided. If you stay at least 24 hours a sissy baby toothbrush will be provided. You may take it home with you. All sessions of at least 24 hours come with a bubble bath complete with bath toys and a character hooded towel. If you're a good girl, Mommy will give your scalp a good scrub with baby shampoo.

Sissy Baby Bathroom   Sissy Baby Bathroom   Sissy Baby Bathroom

Gynecology Office

Gynecology Office



Laundry Room

I am a laundry fanatic, so a beautiful and functional laundry room is essential. Everything used during a session is washed, sanitized, dried, ironed, and neatly folded or hung. I believe it is imperative that a sissy maid be trained in proper laundry procedures, so she can capably perform her laundry duties. I find that a favorite task of many sissy maids is washing my delicates, taking care not to run my silky stockings or snag my precious panties.

Laundry Room

Punishment Parlor

I have a lovely, old-fashioned front parlor for those into domestic discipline, OTK spankings, corporal punishment, et cetera. There is a sturdy straight-backed wooden chair and an unparalleled collection of belts, straps, paddles, wooden spoons, carpet beaters, wooden hairbrushes, canes, switches, birch bundles, nettles, and, of course, my strict hand. If you infuriate me, your time in the parlor will be strictly for punishment. If you need a maintenance spanking, that may be more sensual.

Punishment Parlor



Sissy Training:

Over the years, I've purchased a variety of sissy maid dresses, sissy costumes, sissy slut outfits, sissy baby attire, and sissy accouterments. I love turning naughty boys into cute sissies. Sissies have a special place in my heart. I adore training sissy maids, sissy sluts, and sissy babies. It is impossible to depict my entire collection here, but I will give it a shot.

Sissy Maid Training

Proper training and attention to detail is crucial to creating a perfect sissy maid. Imperfection is not an option. From head to toe my sissy maids are a study in perfection. They flawlessly curtsy. Their attire is impeccably arranged. There is never so much as a crease in their taffeta or a run in their stockings. All my sissy maids are trained in the art of tea service. They undergo rigorous schooling in household duties, such as cleaning, cooking, and waiting. Each sissy maid is assigned one special personal task that is particular to her and only done by another sissy maid, if she is unavailable. If within her limits, a sissy maid may be asked to do outside tasks, like picking up dry cleaning, grocery shopping, procuring drugstore items, and so on. My sissy maids receive my tutelege with regard to hair, makeup, skincare, diet, exercise, and deportment. Vocal lessons to improve a feminine lilt may be given. Learning to properly cross one's legs, make feminine gestures, walk in high heels, and carry oneself in a ladylike fashion is par for the course. Chastity is almost always on the agenda. Those things dangling betwixt a man's legs are a nasty distraction. Sissy maids are much better off caged and focused. Discipline is of the utmost importance. That is why I give my sissy maids clear boundaries, duties, and rules. I teach them the difference between discipline and punishment. Punishment is only meted out when warranted. Some sissy maids benefit from over the counter estrogen creams or herbal supplements, others from prescription hormone replacement therapy. Age is unimportant. Race is unimportant. Religion is unimportant. Height is unimportant. Weight is unimportant. Disabilities are unimportant. Attitude is everything. Any cisgender, non-conforming, or non-binary male who wishes to experience the thrill of being a sissy maid should seek my guidance.

"Your ability to read things in people, that they don't even realize, is phenomenal."
- Belinda (shown below in the Edwardian sissy maid uniform)

Edwardian Sissy Maid Belinda   Edwardian Sissy Maid Belinda   Sissy Maid Belinda

Sissy Maid Belinda   Sissy Maid Belinda   Sissy Maid Belinda

Sissy Maid Belinda   Sissy Maid Belinda   Sissy Maid Belinda

Sissy Maid Lacy   Sissy Maid Lacy   Sissy Maid Lacy

Sissy Maid Lacy   Sissy Maid Lacy   Sissy Maid Lacy

Sissy Maid Lacy   Sissy Maid Lacy   Sissy Maid Lacy

Sissy Maid Lacy Socks   PVC Sissy Maid Jessica   Sissy Maid Jessica

Sissy Maid Jessica   Sissy Maid Michelle   Sissy Maid Michelle

Sissy Maid Michelle   Sissy Maid Michelle   Sissy Maid Michelle

Sissy Maid Michelle   Sissy Maid Michelle   Peenie Petal

Sissy Maid Michelle   Sissy Maid Michelle   Sissy Maid Michelle

Sissy Maid Pink Ruffles   Sissy Maid Marsha

Sissy Slut Training

Sissy Roberta   Sissy Slut   Sissy Laura

TS Trixie   TS Trixie   TS Trixie

Crossdresser Martina   Transvestite Martina   Sissy Slut Martina

Sissy Baby Training

Sissy Baby Jessica   Sissy Baby Jessica   Sissy Baby Jessica

Sissy Baby Jessica   Sissy Baby Jessica   Sissy Maid Jessica

Sissy Baby Mary   Sissy Baby Mary   Sissy Baby Mary

Sissy Baby Mary   Sissy Baby Mary   Sissy Baby Mary

Sissy Baby Mary   Sissy Baby in Chicago   Sissy Baby Jessica

Sissy Baby Jessica in Chicago   Sissy Baby Jessica   Sissy Jessica Wears A Peenie Petal

Submissive Sissy Training

Transvestite Crossdressing Training

Sissy Secretary Marilyn   Sissy Secretary Marilyn   Sissy Secretary Marilyn

Miss Belinda   Miss Belinda   Miss Belinda

Belinda   Belinda   Belinda

Chicago Sissy Slave   Chicago Sissy Slave   Chicago Sissy Slave

Pretty bitch   Pretty bitch   Pretty bitch

Pretty bitch has a very pretty sissy stick!   Helen at Be All   Secretary Jessica

Sissy Chrissy   Sissy Chrissy   Sissy Chrissy

Rebecca Crossdresser   Rebecca   Rebecca

MTF Transformation - Rebecca   Rebecca Corset Heels   Femme Transformation

Sissy Secretary   You can't go wrong with a blue wig and a farmer's tan!

Kinky Gurls

Hogtied Sissy   Hog-Tied Sissy   Sissy Bobbi

Bitch Bobbi   Bitch Bobbi   Bitch Bobbi

Bitch Bobbi   Rubber Doll   Rubberdoll

Electro Play   Electro Play   Electro Play

Secretary Marilyn corseted and helpless!  That's a butt plug harness and a spanked ass!   Secretary Marilyn bound!   Secretary Marilyn in bondage!

Sissy cross-dresser in rope bondage!   Sissy cross-dresser in rope bondage!   Sissy cross-dresser in the pillory!

Sissy crossdresser cheesecake!   Cheesecake on a spanking bench!   Sissy crossdresser in a bondage chair!  

Helpless sissy!   Bound and gagged!   Tied and humiliated!

Now, that's a tuck job!   Ready For Forced Gyno Exam   Bound & Gagged For Forced Gyno Exam

Latex Bondage Sissy   A shaved cunt is an absolute must!   fishnet bodystocking and Latex thigh high boots

She's in for a breast enhancement!   Those C cups are sweet!   Tig old bitties!

Sissy Jessica as a beautiful ballerinal!   Sissy Jessica in bondage!   Sissy Jessica bound and forced!

Sissy Jessica FemSkin   Sissy Jessica in a FemSkin!   Sissy Jessica - FemSkin - Vibrator - 'nuf said?

Sissy Jessica In My FemSkin, Blindfolded, & In Bondage   Sissy Maria in a strait jacket!   Sissy Maria bound and helpless!

Sissy Maria tied with scarves!

Chastity Training

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

CB2000 Chastity   CB3000 Chastity

Transformation Supplies

Drag Makeup   Drag Nails

Sissy Wardrobe

Sissy Maid Wardrobe

Black and Pink Sissy Maid Dress   Lavender Sissy Maid Dress   Black And Red PVC Sissy Maid Dress

Red Floral Trim Sissy Maid Dress   Pink White Polka Dot Sissy Maid Dress   Pink Satin Sissy Maid Dress

Sissy Slut Wardrobe

Sissy Baby Wardrobe

Submissive Sissy Wardrobe

Crossdressing Wardrobe

Slutty Whore Crossdressing Wardrobe

Prim And Proper Crossdressing Wardrobe

Forever 21 haul for the Sissyville Salon wardrobe.

Crossdressing Shoes

Sissy Shoes