Chicago Feminization

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Chicago feminization mistressChicago Feminization is the home of Goddess Madeline, an ultra-feminine professional dominatrix and lifestyle mistress who specializes in FemDom, sissy training, cross-dressing, forced feminization, petticoat punishment, hypnosis, chastity, makeovers, MTF transformations, OTK spanking, erotic humiliation, domestic discipline, female led relationships, small penis humiliation, cuckolding, public humiliation, and much more.

I am a versatile dominatrix. I am extremely sensual, but strict when necessary. I am the most knowledgeable mistress in Chicago, hands down, when it comes to feminization, crossdressing, sissification, hypnotherapy, and male to female gender play.

I welcome everyone from casual cross-dressers to sissy bimbos to those going through MTF gender affirmation.

I offer loving guidance in a supportive and understanding environment. I can also be hell on wheels.

Everyone is welcome, heterosexual, homosexual, bisexual, asexual, pansexual, transsexual, intersexual, queer, polysexual, cisgender, transgender, gender queer, gender questioning, et cetera.

My play space, Sissyville, is located on the northwest side of Chicago and is fully-equipped with an amazing array of cross dressing supplies, bondage equipment, transformation gear, and feminization implements.

My work with the gender play community spans over three decades, first in LA, then Detroit, and now Chicago.

I prefer not to label people, especially with regard to sexual orientation or gender identity. Labels are dangerous.

Live, Phone, & Cam Sessions Available Daily

Live Sessions:

You may schedule a session with me by clicking on the button shown below.
Session Booking Form

Phone Sessions:

You may call me for a phone session through CallJaneDoe, NiteFlirt, or TalkToMe by clicking one of the options shown below.
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Cam Sessions:

You may call me for a cam session through CallJaneDoe, NiteFlirt, or TalkToMe by clicking one of the options shown below.
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Adult Content Warning 18+ Or 21+ Only

This site contains explicit adult content and images of sadomasochistic and fetishistic activities. Do not go any further if you find this sort of mature subject matter offensive. The material on this site is adult-oriented and provides access to images of nude adults. By law, you must be at least 18 or 21 years old, depending on your jurisdiction, to enter this site. Access is made available only to those who accept the terms of the following agreement.

By Entering This Website, I Certify The Following

I do not find images of nude adults, adults engaged in sexual acts, or sadomasochistic or fetishistic activities, or other sexual material to be offensive or objectionable. I am at least the legal age of consent and have the legal right to possess adult material in my community. I understand the standards and laws of the community, site, and computer to which I am transporting this material. If I use these services in violation of the above agreement, I understand I may be in violation of local and/or federal laws and am solely responsible for my actions. By logging on, I release and discharge the providers, owners, and creators of this site from any and all liability which might arise. Bookmarking to a page on this site, whereby this warning page is bypassed, shall constitute an implicit acceptance of the foregoing terms herein set forth. I am not a law enforcement agent, U.S. postal official, organization, or individual working with such an entity attempting to obtain any evidence for prosecution and/or entrapment. I understand that this site is intended for entertainment purposes only.

Title 18, U.S.C. §2257 Record-Keeping Requirements Compliance Statement

All models depicted on this website were 18 years or older when the images were created. All records required to be kept by federal law will be made available, during normal business hours, by Goddess Madeline. All other visual depictions displayed on this website are exempt from the provision of 18 U.S.C. §2257 and 28 C.F.R. 75 because they do not portray conduct as specifically listed in 18 U.S.C §2256 (2) (A) through (D), as amended, but are merely depictions of non-sexually explicit nudity, or are depictions of simulated sexual conduct, or are otherwise exempt because the visual depictions were created prior to July 3, 1995. With respect to all visual depictions displayed on this website, whether of actual sexually-explicit conduct, simulated sexual conduct, or otherwise, all persons in said visual depictions were at least 18 years of age when said visual depictions were created. Questions or comments regarding this disclosure should be addressed to the custodian of records at:
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