Cross-Dressing Made Me A Better Father

By

cross-dressing dad, pirate daughter
One man's evolution from "the guy in the dress" to a candidate for world's most compassionate dad.

Well, this is familiar, I thought as I helped my four-year-old daughter into fishnet stockings and corrected the frankly amateurish lacing on her faux-corset top.

As Taylor Swift sings, "It's the age of princesses and pirate ships," and that couldn't apply more precisely to this bonding moment between the two of us. Luckily, I knew exactly how to assemble a pirate-inspired outfit my daughter would love: something flowy and black, with enough pink to make it girly but not enough to overshadow the pirate aspect. It needed skulls for menace and danger, but a petticoat for the cutesy factor. She didn't make these requests out loud, but I could intuit them.

Beyond being her dad, I am rather uniquely suited for my role as costume designer. For almost half my life, I regularly cross-dressed.

Mostly I did this as a performer. I started as a 14-year-old boy with a local Rocky Horror Picture Show cast, and continued to play Dr. Frank-N-Furter for most of my decade-long run. I had a fantastic costume, too, accurate right down to the most exacting detail, thanks to a seamstress girlfriend with an obsessive streak.

Rocky Horror Picture Show Dr. Frank-N-FurterMy metal-boned bustier was form-fitting with a laced front that showed off a body in great shape from a brief career as a luchador. High-quality black briefs were overlapped by a really kickin' garter belt attached to black fishnets that ended in rhinestone heels. I topped this off with a pair of shimmering gloves and pearl choker. It's an iconic look for a reason, and I enjoyed every minute of it.

This penchant for cross-dressing didn't come out of nowhere, though. In high school, I hosted beauty contests to raise money for the theater department. To that end, I embodied a character I called 'Victoria Massingale,' a bubbly blonde with lots of red carpet wit and a thing for tight, black evening gowns. I became fairly well-known in school as "the guy in the dress."

Little did I know back then that an early career in drag was more  than just a good time: It would give me some of my most valuable  training for becoming a compassionate father to my daughter.

For starters, the practical stuff. I can pick out clothes with her, accessorize, help her find a "look" and guide her towards accomplishing that goal. Dressing as a woman when you're a man gives you a pretty hard glimpse into the ways society expects women to always appear polished. As men, we tend to take that for granted; The level of judgment is inherent. I say that as a guy sitting here with two days of beard stubble and dressed in a Doctor Who t-shirt that I may or may not have picked up from the floor this morning. No one is going to judge me for that, but a woman would be judged both by men and other women.

So is it right that I should be helping my daughter into an elaborate, corseted pirate costume, consciously aware of the imbalanced standards of beauty in America as I do so? No, and I have no idea. I hope to raise awareness of the inequality and help foster change, but in the meantime, she wants to look like her own version of pretty, and I find comfort in the fact I have enough knowledge of women's fashion to help her meet her own standards.

Cross-dressing also helped me break down gender-role barriers. When people asked me if I wore women’s clothes I would usually reply, I wore my clothes. Nothing more. I bought those dresses, those shoes, the wigs, the undergarments. I was the recipient of many prototype costume pieces designed by my then-girlfriend (who went into a side business making cheap, fast costumes for Rocky cast members all across the world). It forced me to look at what makes a woman who she is, divorced of social norms, and that's a wonderful perspective to have as the father of a daughter.

I know lots of fathers that wipe their hands of many of the feminine aspects and milestones of their daughters’ lives. Oncoming menses, bra training, make-up — all that stuff. That's your mother's area of expertise. Call me when you want to change a tire or kill a spider.

Having walked a mile in the shoes of my opposite gender (literally, in my case — and not having fully recovered from those stilettos, to be honest) means that I am simply unable to consider those parts of my daughter's life "off-limits" and dismiss them as a woman's domain. I'm her father, and I should be able to talk with her about anything without getting squeamish, even the things I don't personally experience as a man. Learning how to be comfortable with other gender identities is one of the major steps towards a greater understanding of one another — and a lot less misogyny.

Plus, I like that I can be her fashion buddy.

Oh, and the pirate outfit, with its little fishnets and satin lace top? It killed at the exhibit. People took pictures of her and thought that she was part of the show. She loved every minute of it. It really was a time of princesses and pirate ships for us. I hope it always will be.

More awesome stories about parenting styles on YourTango:

 

GET MORE ARTICLES LIKE THIS IN YOUR INBOX!

Sign up for our daily email and get the stories everyone is talking about.

Must-see Videos
SEE MORE VIDEOS
Stories we love
FROM AROUND THE WEB
  • The average woman requires 20 minutes of sex or foreplay before she can orgasm.