Friday, November 11, 2011 — Chicago, Illinois
It was a pleasant day for November in Chicago as I drove through traffic on the Dan Ryan. My work had finished early, around 2:00 p.m. Traffic was typical for a Friday afternoon — thick but moving because it was still before rush hour.
My mood was buoyant because the weekend was starting early, and my thoughts turned to what to do with the rest of my day.
Winding my way north, my mind drifted to a store in the Lakeview neighborhood that had caught my eye shortly after moving to Chicago six years earlier: Skyscraper Heels on West Belmont. I never had the opportunity to look closely at the window because I was always driving by, but the hot pink awning had grabbed my attention. It featured a logo of an extremely high stiletto heel set against a silhouette of the Chicago skyline — shining bright like the Bat-Signal. My drive-by perusals also noticed another key detail: the awning boasted “Sizes to 15,” which absolutely fascinated me.
My afternoon was free. My wife was working a night shift. I decided it was time to go.
💥 The Thrill of the Forbidden
Typical of Chicago’s main arteries, I could not park on Belmont near the store. I was also terrified to park too close; I didn’t want anyone I knew to recognize my car and witness me entering a high heel store. I parked about three blocks away.
I was excited, nervous, and anxious as I made my way toward the store. Although I had never window-shopped Skyscraper Heels, I had browsed its website and had a general idea of the costs. Leaving nothing to chance — like a digital trail on a bank statement — I entered a liquor store and withdrew $100 from the ATM.
My heart was beating fast and I could feel the butterflies as I crossed the street. I walked in with my head down, nervous and jittery.
An older gentleman with a gentle voice was working in the store. He welcomed me and asked if he could help. My nervousness must have been obvious as I mumbled, “Oh, just browsing.” Sensing my anxiety, he graciously let me be and made his way to the front of the store to draw the blinds, giving me complete privacy.
👠 Stepping Into a New World
The offerings ranged from standard high heels to extreme fetish shoes. Peep toes. Stilettos. Slingbacks. Strappy heels. Boots. Thigh-highs. Black leather, patent, red, pink, and even rainbow.
The choices were overwhelming. A pair of black boots caught my eye, but they were much more than the $100 in my pocket. My attention turned to the classic pumps. The store owner came over again to break the ice. I finally relented and pulled three different black heels for consideration.
He asked my size. “Well, these are size 13,” I said, pointing to my black Allen Edmonds dress shoes.
He suggested a size 14 or 15 in women’s, which matched my own online research. There, in that small store, I tried on a pair of high heels for the first time and took my first steps. Size 15 was too large, as my heel flopped out of the back. Size 14 was better, but my narrow heel still slipped.
Then, I tried a pair of black patent heels with an ankle strap. The strap held my feet perfectly in place. The four-inch heels were a challenge to walk in, but having them on my feet felt fantastic. Sold!
I paid in cash. He placed the shoebox in a plastic bag, and I scurried back to my car. As soon as I got inside, I hastily untied my men’s shoes, ripped off my socks, and wiggled my bare feet inside my new heels. My very first pair!
The precious few steps I had taken in the store were a cakewalk compared to trying to drive in four-inch heels. My left knee jutted up much higher than usual, and the heel kept catching on the floor as I tried to pivot between the gas and the brake.
My wife would still be at home at this time of the afternoon, around 3:30 p.m., so another bold idea entered my mind. I needed a wig. There was a year-round costume store a few miles from my apartment. I crawled through traffic, changed back into my boy shoes, and went inside. I opted for a simple, medium-length brunette wig displayed behind the register.
💄 Transforming in the Shadows
I slowly made my way back to my apartment just after 5:00 p.m. I managed to squeeze the shoebox and the wig into my work bag and went upstairs to see if my wife was gone. She was.
As soon as I knew I was alone for the next few hours, I began a secret routine I had completed many times over the years. Feminizing myself.
I went into our bedroom and picked out a few of her clothes I had always admired: a black sweater dress, a black bra, tights, and a matching pair of panties. I slipped into the lingerie and pulled on my brand-new heels. Then, I gathered an assortment of her makeup: foundation, lipstick, mascara, eye shadow, and eyeliner.
But first, I had to prepare my face. I shaved my five o’clock shadow away in two stages: a normal shave with the grain, and a second pass against the grain to make my skin as smooth as possible.
Walking to the bathroom in my new heels was an absolute rush! I loved the rhythmic, sharp click they made on the hardwood floors and tile.
With my face smooth and prepped, I pulled on the brunette wig and adjusted it in the mirror. Then, I began applying the makeup. Layer by layer, the man from the Dan Ryan traffic began to fade away. I carefully applied foundation and concealer, penciled my eyes with black liner, darkened my eyes with the shadow, brushed on the mascara, and painted my lips a soft shade of red. The result? A seductive cat-eye look that made my soul flutter with pride!
📸 Capturing the Moment
With the look complete, I spent the next hour parading around the apartment, practicing my walk in the four-inch heels until the awkwardness melted into a confident stride. I pulled out my iPhone, desperate to capture this fleeting reality. I took a flurry of selfies from every angle—close-ups of my made-up face, shots of me posed and seated, full-body mirror captures, and a few soft, relaxed pictures lounging on the bed. Seeing myself preserved on the screen made it all feel so wonderfully real.
I stepped back to look at my reflection. For the first time in my life, the person staring back at me didn’t just feel like a man in a costume. With the weight of the wig framing my face and the perfect four-inch arch of my new patent heels anchoring my stance, I didn’t just feel dressed up. I felt entirely, beautifully complete.
