Wednesday, October 22, 2025

Remembering Fantasia Fair

This week is TransWeek in Provincetown, Massachusetts. Previously known as “Fantasia Fair,” I attended 17 years ago and today's post are my thoughts about that amazing week en femme 24/7 in October 2008.

During my week en femme in Provincetown, I shopped, dined, and had many other encounters with civilians throughout Provincetown and never had a problem. Everyone I encountered was friendly and treated me like a lady with one exception. Twice, I bought items at a pharmacy on Commercial Street.

First time, I found what I wanted to buy and stepped up behind a dude talking to the pharmacist who was standing at the cash register. The dude and pharmacist concluded their chat. I stepped up to the counter and the pharmacist turned his back on me and walked away instead of ringing up my purchase. 

I waited a minute or two for someone to ring me up. A middle-aged woman finally showed up to handle my purchase. She was very cold, avoided eye contact and the only words out of her mouth was the amount of money I had to pay.

Second time, the same woman rang me up with the same level of frigidity.

In both cases, I was my charming self, but the only response I received was a blank cold stare. I would not say that the pharmacy was transphobic, but they certainly were not transfriendly and being the only pharmacy in the center of town, I am sure they made a lot of money off the trans folks visiting town last week. Go figure!

***

I improved and streamlined my makeup skills during the week. Doing my makeup twice a day for a week, I found shortcuts to get the job done more quickly. (“Practice makes perfect.”) By week’s end, I probably shaved 15 to 20 minutes off my normal 1-hour makeup routine. I also was able to experiment with different looks and colors, which was a lot of fun!

***

I learned a lot about woman’s footwear during my week en femme. Downtown Provincetwon uses cobblestones for many of its sidewalks and they are unforgiving when you wear high heels. I quickly learned which shoes to wear when I had a lot of walking to do, that is, my booties and my mid-heel pumps with the chunky heel. If I wanted to wear heels at an event, I carried them with me while walking in my comfortable shoes, then changed to heels when I arrived at the event. Luckily, many events were in my hotel, so I did not have to carry heels around town that often.

***

I had a lot of fun mixing and matching separates (tops, jackets, skirts, pants) to create outfits during the week. (Is it still crossdressing when you wear pants?)

***

I reached a new level at Fantasia Fair. Femulating 24/7 for a solid week, you stop thinking about the fact you are femulating and begin living like a woman. All the techniques you use for femulation become second nature; you no longer have to think about using those techniques because they are now natural. I believe that during Fantasia Fair, I came as close to feeling like a natural woman as I can be and I hope that that second nature will stick with me forever.

***

Will I attend future Fantasia Fairs?

As my euphoria peaked at the end of the week, I told anyone who asked that I would be back next year and that I would begin saving money for the trip on Monday to make next year’s trip possible.

After the banquet Saturday night, I began reconsidering my return next year or any year.

The civilians in Provincetown are aware that the circus is in town, which makes it impossible to pass. Every tall woman is a potential man in a dress, so the civilians check out every tall girl to see if that is the case. I never experienced anything untoward in Provincetown, but being a very tall girl, I became annoyed by the inspection that I (and all the other tall girls) had to undergo every time we walked outside.

If you are a closeted femulator and want to get out of the closet in a safe way, I highly recommend Fantasia Fair to you, but I don’t need that. I could take the money I saved to bankroll a trip to Fantasia Fair and have a wonderful time shopping for a new wardrobe in the malls and outlet stores of Connecticut. Sure some people might gawk at me as I shopped, but most would not because (1) they would not be alerted beforehand that a crossdresser may be in their midst and (2) I often pass and do not attract attention to myself in a bad way, that is, in a way that gives away my birth gender.

I had a wonderful time at Fantasia Fair and I am sure I would have a good time if I attended again, but weighing the cost versus the potential of growing more as a woman, I think my money would be better invested elsewhere.

A Connecticut sister hit the nail on the head. During one lunch, she distributed ballots to the Fantasia Fair attendees to vote for the Miss Cinderella Award. Another friend suggested that everyone vote for me, but my Connecticut sister remarked that the purpose of the award is to recognize the attendee who blossomed the most during the Fair and that I had blossomed before attending the Fair.

Nuf said!

[By the way, I attended Fantasia Fair three more times (2010, 2012 and 2014) for the same reason I attended Hamvention year after year: to see friends from all over the world, who I would not see otherwise.]



Source: Rue La La
Source: Rue La La


Christopher Morley
Christopher Morley femulating on television’s Too Close For Comfort.

17 comments:

  1. But wouldn't life be amazing if every day was a 'cocktail dress day' 😊

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    1. No reason it can't be! Or maybe at least we could start slow and turn Casual Fridays into Fabulous Fridays and wear our formal feminine best to end each weekπŸ’ƒ

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    2. mmm now that is a lovely idea -- I've never been a fan of 'dress down Fridays' as it gives the excuse to not make an effort. I think style is very important & we should start the 'Fabulous Friday' campaign ! I'm going to start tomorrow by working from home wearing a long flowing evening dress. Will others join me ? πŸ’ƒπŸ’ƒπŸ’ƒπŸ’ƒ

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    3. Hi Emma, I like your enthusiasm and I hope you do wear your best dress, heels, all the accessories, and feel your feminine best! I have an offsite meeting on Friday and, perhaps instead of my usual panties and nude hose under my pants, I'll choose the much more fabulous (and frisky) garter & stockings.

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    4. I don't know about cocktail dresses, but for me every day is a dress day for me.

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  2. I attended Fantasia Fair back in the early 90's. The Provincetown locals referred FF as "The Tall Ships are in town".

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  3. Is this an old article, Stana? Malls? What is a mall? Nearly all of mine have closed, sadly. Impossible for a girl to shop and actually try things on before they are sent because of differing body shapes. Never thought I'd live to see the day of the demise of your local malls. Holding out hope that they recover, and sooner rather than later!

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    1. Oh, how I miss my local mall! It was the best place ever to eat junk food in the food court, listen to new music in the record store, and walk past all the women's clothing stores and admire all the latest fashions and wish you were wearing them instead of these boring boy clothes...

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    2. Elise, my genesis was wearing female clothes that appeared to be gender neutral but in boy mode before I started wearing wigs, doing makeup, etc. because I wanted to shop but just couldn't in boy attire. I shopped and bought but never really used the changing room until I was en femme. When interacting with female staff, I usually said I was shopping for gifts (Christmas, birthdays) at first and for a period before I really didn't care any longer. Now I don't care at all and relish when I am complimented, including my wonderful fashion sense, which is what happened the other day by a young lady working in the grocery store who went out of her way to compliment me as she was walking past! (I was wearing shin-high boots, a Stana-approved blue jean mini skirt, and a cute short-sleeve top whose colors matched the two minimalist colors in the skirt. Anywho, I still miss the mall and also remember being with people in boy mode and longing after the fashions in the window and probably glaring a bit too long!

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  4. The incident at the pharmacy made me a little sad but the rest of the story more than made up for it! Thanks for sharing all the details. I was vicariously living through you, imagining the ecstasy of living enfemme 24/7 for an entire week!!

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  5. I guess things have improved since October, 2008.
    As from my previous postings, I present "en femme" all the time.
    At no time in the past 9 years I have never been disrespected. At supermarkets I talk to female cashiers a lot, and they are always cordial. And I live in the Dallas-Fort Worth area that is hardly a center for LGB+++
    John

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  6. Please Stana attend Fantasia Fair! Your last 3 visits, 10, 12, 14, coincide directly with the Giants winning the World Series. I definitely think there's a connection. Pretty please?

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  7. It has evolved. I stopped by on Monday for a keynote talk on the history of trans medicine.

    Almost all the workshops are geared toward couples. It seems that all the workshops are like "Alone in Paradise," "Together in Paradise," and "The Wives’ Club." They still have a fashion show, the follies, and a banquet.

    As Stana said, it is a great week to be out and about. The events now are basically in one building, but the lodging is all over town. Plus, you get to walk all over town for lunch at the various restaurants around town. And as Stana also said, many come to visit old friends. I bumped into a couple of "long-timers" at the keynote on Monday. Many of them do not attend the events; they come just to visit friends.

    The town is a mixture of town folk, tourists, and summer residents like me. The town folks are like, "It's trans week, so it must be October." The tourists are walking into doors, gawking at us.

    Now here is a little secret for the locals and the summer residents: the week before is "Women’s Week," and they really know how to party! All the restaurants and nightclubs are still open, and many of them close for the winter because after Trans Week comes Bear Week and the AA Roundup.
    It is me Diana, for some reason I can't log in.

    (P.S. Stana you have been replaced by AI for proofreading)

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  8. I absolutely love that Rue La La outfit! Lauren

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  9. That so strange to have happen in P town. It is such a gay mecca. If they are treating the general population like that they won't be around very long.

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    1. The subsequent three times I attended Fantasia Fair, I made a point to visit that pharmacy to see if my first visit was a fluke, but each time I visited, the transphobia was still there. Being a curious sort, I spoke with other Fair attendees about the pharmacy and their experiences matched mine. So go figure.

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  10. The last picture of the couple in cocktail dresses is terrific. I'd settle being able to spend a Friday evening at home with my wife and I both attired in pretty dresses.

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