08/15/2014 03:05 pm ET Updated Feb 02, 2016

High on Heels

Sometimes a man's gotta do something that's out of the ordinary. Sometimes he has to push himself. Sometimes a man's gotta walk into a shoe store and buy a pair of heels.

My love affair with high heels began in early childhood. Read my HuffPost Gay Voices piece, "Discovering and Outgrowing My Mother's Shoes" and you'll know. That love manifested itself at various stages of my life. My senior year in college I participated in our Theatre & Dance Department's student produced cabaret. That particular spring I performed in drag for the first time in public. Two of my friends and I spoofed a couple of dance pieces that had just been part of our annual dance concert. I played the girl part while my female dance partner in the original piece played the boy part. To complete our menage a trois we added a boy from another dance piece altogether. Incidentally, I had a crush on that boy, but he wasn't out at the time. Memories. I'm off track. Back to the heels.

I went to a thrift store. You know, they were popular even before Mackelmore and Ryan Lewis sang their ode to cheap finds. I was in college and had little money. It's not like I could ask my parents for the funds to buy a fabulous pair of heels. Can you imagine? Anyway, I went to this thrift store and found a pair of black Nine West heels that almost fit. With a little tissue stuffed in the toe they fit perfectly. That was until I put on pantyhose. Wearing pantyhose those shoes wanted nothing more than to slip up and down every time I took a step. How was I supposed to dance in those? Solution. I wore footless nude tights. My ankle area didn't have any hair on it, so I was good to go. With tissue in the toes and sweat created just from wearing them, they stayed on my feet just fine.

Remember on Will & Grace when Karen went to Will's office and made reference to his bamboo shade and the sidewalk level window where he could see bad shoes walk by? Remember how she then lifted the shade and with perfect nasal condescension said, "See. Nine West?" Every time I see that episode I think of those black Nine West shoes. I thought Nine West was upscale, and I'd found a great find at the thrift store. The things I didn't know about labels...I guess Karen set me straight about those shoes.

Then there was the time I worked at a dinner theatre in Florida. I remember finding this fabulous pair of glamorous 1940s-esq strappy sandals. They were gold with thin straps creating the vamp across the toes and a loop for an ankle strap atop the upper heel. These shoes, however, were missing that ankle strap, but I was not deterred. I threaded a gold ribbon through the loop with enough length to wrap it a couple of times around my ankle and tie it. The ribbon blended with the color of the shoes and worked perfectly to hold them on my feet.

I loved those shoes. They even made the move with me from Florida to NYC. There were times my then roommate and I would just put our heels on in our apartment and sit on the sofa talking. He still tells the story of how he liked to put his heels on to vacuum. He was a 1950s housewife in a previous life minus the pearls.

One of my favorite things we did in our heels was sing the two big Daisy and Violet songs from the musical Side Show. "Who Will Love Me As I Am" ended the first act and "I Will Never Leave You" was the 11 o'clock number. For those of you who don't know, Side Show is a musical about siamese twins Daisy and Violet Hilton who became famous stage performers in the 1930s. Emily Skinner played "Daisy" and Alice Ripley played "Violet." I always sang the Daisy role with my roommate singing Violet. I remember this one time (not at band camp) that I was working the cash register at The Drama Book Shop when it was still located on 48th Street at 7th Avenue. I looked up and there was Emily Skinner standing in front of me waiting to pay for a book. I had no filter and proceeded to tell her that my roommate and I sing Side Show all the time, and I always sing Daisy. She didn't exactly look annoyed, but she certainly didn't seem impressed when she replied, "Okay," with a tone of this-is-weird-but-whatever. She paid and left. I wonder if it would have made a difference in her reaction if I'd told her about the shoes? Nah, probably not.

That brings me to present day. I've been wanting to buy a pair of heels for more than two years. A friend of mine has a pair of Jessica Simpson's that actually fit me, and I found myself wearing them almost every time I went to her apartment. It didn't matter if we were eating, sitting on the sofa talking, watching TV, or playing a game. I would put on those bronze-colored heels and just exist.

Here's the thing I discovered about myself. I have a lot of strength and courage for many things in my life, but I was finding it very difficult to access my courage and walk into a women's shoe store by myself and ask questions of the employees. For instance, I needed to know what size shoe I would need. I'm a size 8 in men's, but was uncertain what size that translated to in women's. I think those Nine West heels from college were a 10, but I'm done with stuffing anything but my toes into the toe box of a shoe.

After exhausting my search for someone to go shoe shopping with me I decided that I had to go alone. I knew I could do it, I just didn't want to. I needed the confidence boost of a wing man.

There might as well have been a disco ball hanging above the store to indicate I'd reached my destination when I found myself in front of its window. I looked through the glass and saw shelves of shoes from floor level to the height of stretch-up-to-reach-it. So many shoes. I had to refrain from singing an chorus of "Let's get some shoes." I would have probably been as giddy as a school girl finally being asked out by the boy she'd been crushing on for month if I'd been with someone, but I was alone and a little apprehensive.

High on Heels was the name of the store and I was high. I was in shoe heaven. I was surrounded by closed-toe shoes, peep-toe shoes, strappy sandals, etc. Tall heels, short heels, platform heels, and wedge heels floated on boxes around me. The colors ranged from fleshy beige to deep red with a spectra of blues, purples, greens, and yellows in-between. Some were glittery and sequined in silver and gold. Some were satins in champagne and peach. There were enough glittery reds that Dorothy could have clicked her heels three times in each pair and had enough trips back to Kansas for a month.

"May I ask you a question?" I asked the man who appeared to be the manager.

"Of course," he replied.

"I wear a size 8, but have no idea what that would be in women's."

"Probably a 9-and-a-half or 9."

Supplied with the answer to my size question I set out to find that pair of shoes that would make my eyes wide like finding the perfect surprise under the Christmas tree. My desire was a beige-colored pair of round toe stiletto pumps. You know the kind that have a high heel and a platform in the front. Yep. That's what I wanted. I live in NYC, the home of Carrie Bradshaw and the Gossip Girls. No kitten heels allowed. Besides if a man's gonna walk around his house in a pair of heels he might as well rock a fabulous pair with height.

I found a champagne-colored pair in Five-and-a-half inch heel in back, one-and-a-half inch platform in front. They were pretty fabulous. I took my sneakers and socks off right there in the store and tried them on. After my earlier conversation with the manager, and after noticing that no woman in the store was paying any attention to me, I felt a sense of relief and almost no anxiety over trying the shoes on. I then talked to the manager about how they fit and began testing my balance. It's interesting how one can rock forward on the front platform.

"Will this heel bear my weight?" I asked the manager, thoughts of the denizens of Kinky Boots in my head and their discussion of how the heel on a woman's shoe isn't designed to support the weight of a man.

"Yes," he responded with a look on his face that I trusted.

I was so happy after finding a pair so similar to what I'd wanted that I couldn't resist looking at another pair. They were even more fabulous than I had allowed myself to hope to find.

Sitting atop a display box was a pair of dark mint green, peep-toe, faux-suede, Mary Jane stiletto's with a skinny gold heel. The heel was 6" high with a solid 2" platform in front. They were beautiful. Honestly, I wish the heel was the same color as the shoe (and I would prefer silver to gold), but still I wanted to do my very best Carrie Bradshaw impersonation and say, "Hello, Lover!"

There was a size 9 and whaddya know, they fit me and they were on sale. The truth is I loved them more than the first pair, but decided there was nothing wrong with buying them both. Options, darling! I may only be wearing them around my apartment, but that doesn't mean I have to limit myself.

The cashier who rang me up said she loved the mint green pair but no matter how much she tried she couldn't walk in heels that high. I knew I was going to be able to walk in them, but pretended that I was hoping I could find my own balance.

I was empowered with positivity and courage after walking out of that shoe store. I sent pics of myself in both pairs to many of my friends. (I wore the green ones for at least 3 hours that day). One of them responded to me, "You're an inspiration." I was taken aback. I don't see myself as an inspiration to anyone, but the truth is, he and I had talked about my lack of courage to go into a women's shoe store alone and buy a pair of heels the previous night. Now I was showing him that I had done it. To him, I was an inspiration.

We never know how what we do or say can inspire someone else. I found my courage. I walked into the store, apprehensive at first but determined. I tried on the shoes in the store and had a good laugh with the cashier while buying them. I proved to myself that I can do it -- not just buy high heels, but anything -- and I was rewarded with positive outbursts of pure joy, excitement, and encouragement.

We can get everything we want out of life if we just take the first step. I'm still learning that. Find your freedom. Live your truth. Express yourself however you want. Hold your head high. Walk tall. I am. My steps just happen to be in 6" heels sometimes.

This piece originally appeared on QBlog's Queer Voices page.