Sometimes Dreams Come True

Attending Fantasia Fair in 2010, I became friends with

trans advocate Ethan St. Pierre, who received the Fair’s

Virginia Prince Transgender Pioneer Award that year.

I began crossdressing in my teens in the 1960s. Home alone, I dressed, but I was strictly closeted and even missed an opportunity to Halloween crossdress when I refused my best friend’s invitation to be trick or treating girls.

I continued crossdressing as a 20-something throughout the 1970s. I was still closeted, but got up the nerve to Halloween crossdress on three occasions (and had the time of my life doing so).

Along came the November 1980 issue of Playboy containing an article about Fantasia Fair. It was intended to be a humorous piece, often at the expense of the folks attending the Fair. 

Put that aside, I had never heard of Fantasia Fair and the article provided a trans public service by revealing the Fair to me (and to probably hundreds of other girls like me across the USA).

What a dream! And the Fair was on Cape Cod – an easy four-hour drive, so maybe I could attend and live as a woman for a week. But...

👩 It was not free and at the time, I was only making $10,000 per year. 

👩 I was still mostly dressing out of my mother’s closet, so I didn’t have anything close to a wardrobe for a week (and Mom was not likely to let me borrow hers).

👩 I was scared. Except for a handful of Halloween crossdressings, I had never been out among the civilians and I was ill-prepared to spend a week en femme among the population of Provincetown.

So I did not go. 

Attending Fantasia Fair remained a dream for over a quarter of a century until I finally attended in 2008 (and again in 2010, 2012 and 2014). During the ensuing 25 years, I had joined a support group, attended long weekend trans conventions and went out solo en femme among the civilians, so the population of Cape Cod was no longer something to fear. 

I had a fabulous time each time I attended Fantasia Fair. Living 24/7 as a woman was initially thrilling and then became routine, but in a good way. I attended informative workshops, dined on fabulous food, enjoyed beautiful Provincetown and made a lot of friends.

The Fair is this week and I will not be attending, but I have my memories and they are all good.

Caveat Emptor: This post is an edited rerun of a post from last October.

Wearing New York & Company

Donald Dillaway femulating in the 1934 film The Circus Clown (starring Joe E. Brown)
Thanks go out to Lou for finding this image.