More Comfortable Being Myself

Missy Goes to Prom

By Missy

Femulate readers might know, I have been blessed multiple times with the opportunity to present en femme as Missy while chaperoning my school's annual prom. The 2026 prom marked my fourth such occasion, and Stana has graciously allowed me to share my story after the event each year. (Those interested can easily search the Femulate archives for the three previous installments.)

The mental preparation is admittedly a yearlong process for me because prom is such an iconic event and I want my presentation to be as perfect as possible. There are countless dresses and shoes that catch my eye during the months leading up to the event, and I understand exactly how many of my students feel as the big day draws nearer. Now at more than three times their age (!), I try to temper my outward enthusiasm a bit, but I can't help sharing their joy when they tell me about their preparations. Plus, after a femulation or two at school events each year, many of my students already know I'm almost as excited as they are.

The Wig

Way back in the fall, I took what I consider a big step by making an appointment for an in-person wig consultation and purchase. Because I don't venture out in Missy mode as much as I would like (I'm still working on that—help!), I definitely had prom in the back of my mind when deciding what I was looking for.

In hindsight, I should have taken the time to write up the entire wig saga to share with Stana's readers because it was a tremendous and memorable experience. I absolutely recommend taking the leap and visiting a wig shop in person rather than simply buying online.

If I may plug the location here, anyone in the West Hartford, Connecticut area should definitely stop by Nationwide Wig Imports. They have thousands of high-quality wigs, and the owner, Rebecca, is a gem—patient, honest, knowledgeable, and never pushy. She spent more than two hours with me, offering suggestions and bringing out dozens of options until we found the one she described as "perfect ... very girly in the best possible way."

During the session, she asked what name I used (since I hadn't mentioned it when making the appointment) and then referred to me as Missy throughout the consultation, which was extremely affirming.

And for what it's worth—which is a lot in this instance—if you're like me, you treasure the occasional compliment. As I tried on multiple wigs and paced from mirror to mirror, I chatted with another customer who absolutely made my day ... probably my year ... when she said:

"Girlfriend, you have such a pretty face, you could wear any of those."

I asked if I could hug her, and she accepted.

The Dress

My wife tolerates the amount of closet space Missy's wardrobe has claimed, and I admit I probably own too many dresses. Then again, what I really need are more occasions and locations to wear them—and the courage to make those occasions happen more often.

I frequent local consignment stores, regularly search the sales racks at Macy's, and keep an eye out for deals on apps like Gilt and Rue La La, so I haven't broken the bank on any one dress. Still, the quantity certainly compensates for the reasonable prices!

Because my style could best be described as very feminine (mostly dresses and very few pants), I had several possibilities for this year's prom. To narrow things down, I asked a couple of friends—the married couple whose pre-wedding event I attended as Missy last year—if they would be willing to come over for dinner and a fashion show. My wife is a phenomenal cook, and they are amazing friends, so it was an easy request to fulfill.

I won't bore you with all the details of the fashion show, but I tried on roughly ten prom-worthy dresses. When I came downstairs wearing the dress shown here, my friend (a former model) casually said:

"Okay, we're done. Nothing more to see here."

It was my favorite dress, too, and my wife ranked it near the top of her list, so I was thrilled we were all on the same page.

The gown is by Rene Ruiz and was purchased during a huge clearance sale on one of those aforementioned apps. The photo shown here was taken at the main entrance to the prom while I was officially "on duty" as a chaperone.

Later that evening, I texted the photo to my friend (the other half of the couple I mentioned above). His response:

"Showed my daughter your full-body solo photo and her response was immediate: 'OK, hot AF!' She would also like to know where you got the dress."

I'm not sure a teenage girl could have paid me a higher compliment. Another "made my year" moment.

The Shoes

Similar to what I said about dresses ... I probably own too many shoes.

(Wait—is there such a thing?)

Even so, after settling on the dress, I wandered into DSW a few days before prom just to see whether anything caught my eye.

Sigh.

You know how it is.

Even though I already owned a couple of pairs of sparkly silver sandals, I simply couldn't resist these: Mix No. 6 sandals with a 3.5-inch flared heel ... and, once again, on clearance!

When I brought them to the register, the young man behind the counter rang them up, looked them over, and asked skeptically:

"Are these a gift for someone?"

I replied:

"Yes. They're a gift for me."

I'm not sure how I would have answered a few years ago, but I'm beyond trying to cover things up in moments like that. It takes too much effort. And as many people have noted on this website, salespeople are rarely judgmental when a sale is involved.

Heck, if a salesperson really needs validation, I'm fully prepared to show them photos of Missy!

The Prom

Unlike last year—when I had to bring my entire transformation to school in a duffel bag and change into Missy in the faculty bathroom—the schedule this year allowed me to leave school early and get fully prepared at home.

The transformation went smoothly (no nicks or cuts!), my glittery silver nails matched the dress and shoes perfectly, and my makeup was as on point as I could make it.

After my wife took a few photos and I texted them to our three kids, I tossed everything I needed into my purse and drove (close to the speed limit!) to prom.

On the way, I received a text from my non-binary child that read:

"I hope prom goes well. You're a really great and inspiring dad :)."

There was no better feeling. They are one of the reasons I have become more open about Missy with my students.

When I arrived at the venue, most students had not yet shown up, so I spent time chatting with colleagues, who were nothing but complimentary, and, naturally, posing for a few more photos.

A rather robust wind sadly took its toll on my hair, but otherwise the evening was perfect—from the weather to the music to the students' manners and deportment.

My colleagues and I divided up the chaperoning duties, but it was an easy assignment. I consider myself very fortunate to express myself in a community that doesn't think twice about my presence being part of its prom celebration.

My Stories from Prom

One colleague asked what I used for breast prosthetics, to which I honestly replied:

"Errrrr ... nothing other than a bra. This is all me. Why?"

She said she was impressed by how the dress fit and explained that her father worked in prosthetics.

"If you ever need anything, let me know."

I've only briefly considered adding something like that to my appearance, but never say never.

While chatting with a group of parents, I greeted one student's mother.

"Hi, how are you?" she replied before continuing her conversation.

After listening for a few minutes and contributing a few comments of my own, her eyes suddenly widened and she covered her mouth.

"Oh my God! I was so mad at myself because I thought I knew every mom here and couldn't place who you were!"

She gave me a big hug and complimented my look. Another mom asked what brand of lip gloss I used because she was "jealous of how my lips shined."

For the record, after checking my purse, the answer turned out to be e.l.f.

Finally, another student's mother asked point blank:

"So what name do you use when you're dressed? There's no way this is a one-time thing."

The question caught me off guard, but there was no reason to be evasive.

"Missy," I answered.

"I knew it. You look amazing, Missy."

Then she added:

"That wig is exactly the color and highlight pattern so many of us are trying to achieve at our age."

We laughed, and she then showed me a photo of the drag persona of her older son, with whom I had worked several years ago.

He looked absolutely fierce and completely unrecognizable.

More importantly, it was a wonderful moment of solidarity that I deeply appreciated.

Closing Thoughts

Whew. I think that sums up this year's prom story!

Over the past few weeks, several snippets on Femulate have really resonated with me, including these:

"Confidence is usually more feminine-looking than panic."

"At some point, many crossdressers realize that the goal is not necessarily fooling everyone. The goal is simply existing comfortably in the world while presenting femininely."

And I often return to one of the most important lines from Kandi's Land:

"Be smart, be appropriate, be confident and, above all, be visible."

I am going to do my best to work on the visibility piece during the coming year, but I will continue drawing motivation and inspiration from Stana's readers, contributors, commenters, and those at our sister sites.

Thank you so much for reading.

I'll close by slightly paraphrasing another wonderful line from one of Stana's recent articles—one that perfectly sums up my prom experience:

"The goal is never to become someone else. The goal is simply to become more comfortable being myself."

Amen to that.

Wearing Shein

J. B. Morgan femulating as a flower girl in a womanless wedding, Nashville, Tennessee, 1918.