NYC En Femme

By Missy

Up until a few weeks ago, the only times I had been out in the wider world as Missy were 1.) Halloween parties (always the easiest outlet for presenting en femme) and 2.) special “themed days” or events at the school where I teach including the past two proms, as some of Stana's readers are aware. My school is an overall accepting and supportive environment where I can usually be whatever version of me feels right.

This past winter, however, a very good friend invited me to attend his upcoming wedding, which was to take place in April in New York City, as Missy, if I wanted to. I had chaperoned the prom with this friend for many years (and he was essentially my “date” for the past two), and his fiancee is equally comfortable around me as Missy (and has even loaned me a couple of her outfits!), so there was no question about being supported if I wanted to take what certainly felt like a big step.

Attending a wedding en femme was a “bucket list-level” opportunity, right?! But after giving it some thought, I declined the offer because my wife would be attending the wedding with me and although she is tolerant of my exploits as Missy, this would have been a huge ask. Plus, despite my friend suggesting it, I couldn’t help but think Missy’s attendance could have been a potential distraction.

The wedding couple completely understood that decision, but then added that there would be some pre-wedding events in NYC the day before the ceremony, one of which was (wait for it ...) a drag brunch! What better place for Missy to make an appearance?! So after having read so many positive out-and-about stories on Femulate, Kandi's Land and other sites for years, and talking it over with my wife (who would not be attending any of these events), I decided that yes, Missy would indeed venture from suburban Connecticut into the big city for the drag brunch and the family/friends gathering afterwards. (*gulp!*)

The first order of business was obviously picking out what to wear. With the help of the bride-to-be, my wife and another friend, we decided the “draggiest” outfit I had was this sparkly jumpsuit from H&M (proudly purchased for $3 at a garage sale last summer).

Found coordinating jewelry, had the right heels and was feeling more positive as the date drew nearer and then, a couple of weeks before the event, my friend dropped the bomb that the drag brunch was CANCELED!! 

NOOOOOOOO!!!!!! There aren't enough exclamation points to do justice to what had just happened! I felt bad for my friends, of course, because they had planned a fun event for about 40 individuals that had to be scrapped. But they also felt bad for me because they knew I was looking forward to my first truly major outing as Missy. Wanting to still have an enjoyable “Plan B,” they replaced the drag brunch with a gospel brunch at the Blue Note Jazz Club in Harlem.

Then came the moment of truth. I was still planning to attend the event, but as Missy? A drag brunch seemed like a pretty safe haven. A gospel brunch? I honestly wasn’t sure. I waffled for a few days (Yes, that was a brunchy reference) and talked it over with my wife. Ultimately, we decided that my “pink fog” was already pretty thick, so Missy was still going to New York! (*gulp" again)

Once that was settled, this meant a different outfit! Actually, I decided on two outfits, one for the gospel brunch and another for the gathering in the hotel afterward. Surely a wardrobe change was warranted if I was going to make this experience as memorable as possible! I wore a Boho-style dress to the jazz club and a denim-ish dress to the later gathering.

There was no way I was going to ride the train solo as Missy, so I traveled in “standard mode,” met the couple-to-be at their hotel room beforehand, made the transition into Missy and then a group of about 20 of us walked to the subway. As the saying goes, there is safety in numbers, and I felt relieved and comfortable being part of the larger pre-wedding posse. I chatted with the mother of the bride and the mother of the groom most of the way to the jazz club and there were no issues whatsoever regarding my presentation as Missy on the streets of NYC or on the subway. In fact, I received numerous compliments from strangers on the subway about my dress (and on my fingernails and toenails, which also made me feel good!). 

At the hotel gathering later that afternoon, after changing clothes and fixing my makeup, I felt even more comfortable, had normal conversations with both friends and strangers, was told I looked “ravishing!” by a former student and just enjoyed my brief but memorable time mingling as Missy. My wife and I traveled down to NYC the next day to attend the wedding and everything felt right in both parts of my world. [:-)]

Listen, readers, I know I didn’t completely pass, but I honestly didn’t expect to. This was more about simply letting out that part of me anyway, and doing what felt right. As we have read countless times on these websites, being confident is the most important thing and people are more accepting than we give them credit for. (In the dark of the jazz club, though, I'm confident I passed a bit more easily because I had to “introduce” myself to a couple that I have known for close to 20 years, who did not recognize me at all)

If/when the opportunity presents itself, I will feel less hesitant to take a journey as Missy. I get daily positive vibes from many of you on Stana’s site (Stana! Norah! J.J.! Too many others to name!), so thank you for your ongoing words of wisdom.

Thanks for taking the time to read. Stay tuned for the upcoming story from Missy's Prom, 2025!

Wearing Boston Proper

Anson Williams and Ron Howard femulating on television’s Happy Days.