Chicago Schoolboy DisciplineHome


This web site, Chicago Headmistress, explains the philosophy of Morningwood Academy and Headmistress Madeline.  Madeline is a schoolmarm dominatrix, in Chicago, who specializes in corporal punishment, academic discipline fetish, behavior modification, educational fantasy role-play, and related lessons. Her space, Morningwood Academy, is located on the northwest side of Chicago and is fully-equipped with an amazing array of schoolroom furniture, study hall decor, and scholastic discipline implements intended for naughty adult students.  Madeline is a very strict schoolmistress who demands perfection from her students in her fantasy classroom.



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Phone Sex Domination Domestic Discipline


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 material 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.


I do not find images of nude adults, adults engaged in 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.


All models depicted on this Web site 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 Headmistress Madeline. All other visual depictions displayed on this Web site 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 Web site, 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:
Headmistress Madeline of Chicago


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Eros Chicago Fetish / Fantasy
Eros Chicago Fetish / Fantasy