A Day Out and About… In Heels

June January 16, 2023 Crossdressing Experiences 58

This is a multi-part story. I hope you will vicariously reminisce, explore and/or envision being right there with me as it unfolds…

If you’re close to my age, you’ll recall Dragnet’s Sgt. Joe Friday implore female informants to provide “Just the facts, ma’am.” The story you are about to read is real, and these are the facts…

I’ve not attempted to train my voice. It is what it is. Compared to Weather Channel forecaster Heather Tesch, it’s not so bad. Back in the day, I shopped in drab using my “twin sister” as an excuse. BTW, I don’t have a real twin sister. Then online shopping became available. And when I finally stepped out En femme, I only used self-checkout kiosks at the grocery store to avoid the attended checkout lanes because I feared having to speak… or be “made” as some would say. That was then. Now, I decide which lane to use based on what I have to check out and how much time I have. But what’s my voice got to do with a day in heels?

This story takes place on December 23^rd. Two days before Christmas, and the eve of the winter storm, Elliot. I did my grocery shopping before Elliot laid siege. It was cold, but not frigid, so I wore my ¾ length leather jacket. It was perfect for the day. I wore a light purple satin blouse under it with black pants and black pointed toe, slingback, kitten heels. I’ve studied videos of myself in heels to master the walk. I’ve practiced in the garage and around the house and up and down stairs. I’ve worn heels out with every intent of wearing them for the day. But, when I got to my destination, I chickened out and changed into flats. My day out-n-about itinerary included a chocolate shop, the mall, and the grocery store.

A new chocolate shop has opened in the Rose District in Broken Arrow, OK. It specializes in Belgian chocolates. If you know your chocolates, you know Belgian chocolate is only processed in Belgium and known for its luxurious smoothness. Hoping to visit this shop with a CDH friend earlier this month, I had sent a message to the owner stating that I was a chocoholic… and a crossdresser. Not that one has anything to do with the other, but I thought it would grab the owners’ attention. I asked if he would be comfortable with a couple of crossdressers in his shop? I felt certain that would get his attention. I stated we were both classy, casual dressers and that if we were any good at this, he wouldn’t recognize us from his other customers. As hoped, my shock and awe worked. I received an almost immediate reply that we would be welcome, and he looked forward to meeting us.

The shop is in a revitalized downtown shopping district. I found an open parking spot a city block from the storefront. Wearing my heels, and with a smile on my face, I walked to the store. I window shopped along the way, passing several couples out doing their Christmas shopping. On entering the shop, I noticed it was small, and a lady was completing her order. As she turned to leave, we exchanged smiles and season’s greetings. I stepped up to the counter, where an extremely attractive young lady greeted me. I asked for descriptions of the offerings and then placed my order. We chatted about the wonders of chocolates. There was no sign of hesitation or amazement, no double-takes on my appearance or voice. There were no dubious looks. As she filled the box, I told her it was to be a gift, and she offered to wrap it with a bow. These chocolates will be a gift to my wife from June with a note that it is to be shared with me… my male persona. The store owner came out from the kitchen and spoke with the young lady. After which, I asked if he was Melvin, the owner? He said he was, and I introduced myself as June. He made a queried look and said, “You wrote me an email?” I said I had, and that I was pleased to be welcomed, commenting on how cute his shop was. He was pleased to meet me. I felt welcome and very comfortable standing in his store… in heels. It was a wonderful experience! I felt perfectly comfortable with my presentation and our conversations. I don’t think I wobbled too much… I hope my friend will join me on a return visit…

My next stop was the Mall for some LTDB-ing (Look, Try, Don’t Buy). When I arrived at the mall, the only available parking spaces were the farthest from the building. It was a hike to the entrance. It provided me with more practice in the art of “walking in heels.”

The mall was busy with people scurrying about. It was exciting to be among that many people. I wondered if anyone would single me out. My wife tells me I look like her husband in women’s clothes. Which is the same as telling me I look like a dude in a dress… Sometimes she is not at all encouraging. She won’t look at me En femme, but she will look at my photos and offer suggestions to improve some element of my appearance. She is an enigma!

JCP was my first stop, then on to Macy’s. I’ve learned to hold my head up and walk with confidence… especially in heels. With my head held up, I pointed my heels toward JCP looking at passersby eye to eye. I started at the formal gowns. However, nothing impressed me, so I passed on trying any of them. Next, I sifted through the party dresses, and then all the other dresses. A store clerk asked if I was finding what I was looking for? I said, “I don’t know what I’m looking for, but I’m having fun searching for it.” It was fun cruising through the racks and mingling next to women as they searched the selections. A few I pulled out to examine closer got rave reviews from some of the women. There were a few men looking through the racks, too. I wondered if they were using their wives as excuses, and really looking for themselves? What a perfect opportunity for those who are deep in their closet. Many of us have been there. I have a story to share with you about that, too. Only it wasn’t my wife I used as an excuse; it was my “Twin sister.” I moved on to Macy’s and had the same experience. I didn’t see anything I wanted to try. Nobody talked with me, but I felt as though I was being scrutinized. I didn’t get that at JCP. When you look like me, it happens. I have definite male characteristics which neither clothing nor makeup conceals. Or, it may have been my gait. Regardless, I amazed myself by walking in heels!

I’ve spent about four hours out-n-about…in heels! The day was filled with wonder, excitement, and joy! I talked with people, mingled with women, and wore and walked in heels all day. The enjoyment I get from my times out-n-about is built on confidence. It comes from encouraging comments to photo posts and conversations with CDH friends and members… and from mustering the courage to step out the door.

I am still learning about this thing we do called crossdressing. My wife and I have identified elements of my crossdressing which need improvement. Wearing heels and speaking are two of those.

With my wife’s assessment in mind, I challenge myself to become the image I envision. I’m continually working to improve my presentation, building the confidence to present June with poise. I acknowledge June is a living force within me. And with a vision of who I want June to be, I accept I am my own kind of beautiful.

Please join me for the next installment as my adventure continues at the grocery store…