Academy Herstory: Truth in Advertising

When people ask what inspired me to create Miss Vera’s Finishing School - the world’s first crossdressing and transgender academy - I like to say, “In this town you have to be versatile.”

My dream in New York was to be an author, but I made a few detours. In 1989, after a decade exploring my own sexuality and everyone else’s as a porn star and a journalist with a monthly column documenting the erotic life of New York, I felt ready to write a book I tentatively called “What I learned in the Sex Biz.” In order to finance the writing of that book, I began to help those who identified as crossdressers with their transformations from male to female. How did I spread the word? The Transvestian was a tabloid newspaper dedicated to crosssdressers. It was sold on some newsstands in Manhattan and when I began Miss Vera’s Academy, The Transvestian was the first place I advertised.

From the appearance of that first ad my phone began to ring off the hook. At the other end of the line were “the often nervous, usually husky, sometimes breathy, mostly polite, and always excited voices of the Stephanies, Joanns and Denises…those who had been raised as men who wanted to find the woman inside.”* A year later, I decided to try a more mainstream publication by submitting an ad to New York Magazine’s “personal services” a classified back page that included massage parlors, escorts and houses of domination. My school was already named Miss Vera’s Finishing School for Boys Who Want to Be Girls, but as the magazine’s fees were based on word count, for the ad I shortened the name to Miss Vera’s Crossdressing Academy. Simple and effective, or so I thought. I was immediately rejected by the monitors of that section. Crossdressing as a term and an activity was a no-no on those pages and the word transgender was hardly in use and barely understood. I knew that plenty of crossdressers were visiting other advertisers - the dommes and escorts- and their needs were not being taken as seriously as I offered in my academy curriculum. In most cases the “dress up” consisted of little more than some tacky lingerie. Forced sissification and humiliation were often part of the scenario.This was just the opposite of what I offered. I submitted a revised ad that didn’t mention the taboo word “crossdressing”, “Explore your dreams in an uplifting environment.” The second rejection came swiftly. “Now we know what you do, so you cannot advertise.” I sat down and wrote the New York editor-in-chief a letter, highlighting the benefits of my project to a niche and eager clientele. I waited for a response, but none came.

Original brochures and business cards from Miss Vera’s Academy

In the meantime, my dear friend and mentor fashion designer Ms.Antoinette was coming to town to participate in the Retail Expo at Javits Center. Antoinette had been hugely instrumental in my education regarding all aspects of kink. I decided to throw a party in her honor. I was running my academy classes in the apartment I inherited from my husband which some friends, including early deans (academy instructors), were transforming into a pretty pink studio. With all the work that was being put into the place, I thought “Why not throw a party for the Academy with Ms. Antoinette as guest of honor. I had some reservations. My ultimate goal was to continue my career as a writer. I had only begun the academy to help finance that 1980s memoir. I thought if I call attention to myself with this crossdressing business, it’s such a flamboyant occupation, maybe no one will ever think of me as a writer again. But no publisher was knocking down my door, moreover, I was having fun with the academy project, bringing a subject out of the darkness into the light. With the help of my “Dean of Details” Miss Viqui an illustrator, I created a beautiful brochure with a portrait by Eric Kroll of me in wings as “Cinderfella’s Fairy Godmother”

Cinderfella’s Fairy Godmother - Photograph by Eric Kroll

There were also photos of students who consented to be “our academy supermodels”, like Jennifer James in a corset and pouffy crinolines, photographed by Annie Sprinkle.The academy had already begun to capture people’s imaginations. Jennifer and two other academy students, April and Raquel, begged to serve the party as French maids and I agreed. One of my best friends showed our spiffy brochure to George Rush, then a freelance reporter. George pitched the story of the academy and our launch party to his editors at New York Magazine. A different breed from the ad takers, they were intrigued by the story. (Perhaps my letter to the editor had helped). When they learned “guys in frou frou outfits” would be our French Maids they asked if they could send a photographer. My friends and I were far from camera shy. We were media whores! As for the maids Jennifer and April were fine with photos; Raquel said “Just my legs.” The result was a full page illustrated story that appeared in New York Magazine’s Intelligencer section in February, 1993.

Shortly after that story appeared, I went back to the personal services section and in a perfect example of the right hand not knowing what the left hand was doing, the monitors repeated “We’ve already told you we won’t accept your ad” I immediately referred them to our fabulous story on the Intelligencer page of their very own magazine. I was allowed to place an ad with the full name of my academy. I ran my ad a few times, but by then, I didn’t really need it. That editorial story initiated a publicity snowball that brought print, tv and radio media to our doors. More and more individuals called to schedule our private lessons. Courses ranged from a couple of hours to femme intensives that ran a couple of days. For the callers who were sincere but for various reasons might never attend in person, I created pre-recorded phone lessons. I offered a menu of eight lessons in such courses as “How to walk in high heels”, “How to apply lipstick” “Who is your femmeself?” Callers paid $2.99 per minute. This gave the student a more economical experience and helped subsidize my work. Those phone lessons would become the basis of my first book. Miss Vera’s became known internationally and gender explorers began to visit from across the country and around the world. Every continent was represented in our student body save for Antartica and Oceania. Myself and the academy deans continued personal classes for the next thirty years, during which time I wrote three books based on the school: Miss Vera’s Finishing School For Boys Who Want To Be Girls 1996, Tips, Tales and Teachings from the dean of the world’s first crossdressing academy; Miss Vera’s Crossdress for Success, A resource guide, 2002, and Miss Vera’s CrossGender Fun For All, 2016. All are still available. Though some of the terms have changed, the ideas are still relevant - perhaps even more so. In all of my writing, I’ve emphasized the ways in which nature and nurture, advances in science and medicine, societal stresses, religious repression and more all intersect and contribute to our understanding of gender in the present moment.

Cover of ‘Miss Vera's Cross-Dress for Success: A Resource Guide for Boys Who Want to Be Girls’ Illustration by Glen Hansen

As for the memoir of the 1980s I’m thrilled to be completing that book now and I’m excited to be sharing my stories and memoir previews with you, my substack readers. Meanwhile, my papers are safely preserved at the Schlesinger Library of Harvard University. The history of our Academy, its students, the deans and our early influences are preserved at that other fine academy for the education and edification of all. These days, as fear mongers try to erase the progress made to acknowledge the lives and the rights of transgender folk, preserving that history is more important than ever.

I hope that history gives courage to the many who still live in the closet, and inspires the next generational shift away from an outdated and imposed gender binary. The censors could not stop my Academy’s progress 30 years ago - we are part of a movement whose time has come.

*Excerpts from my first book Miss Vera’s Finishing School for Boys Who Want to Be Girls, (Doubleday,1996).