A Day Out and About… In Heels, (Continued)

June February 15, 2023 Crossdressing Experiences 54

Previously, I’ve been out-n-about in heels visiting a chocolate shop and doing the LTDB thing at the mall. I needed to get to the grocery store before the weather affected travel…and would make walking in heels more treacherous.

As the story continues, I left the mall and was driving to the grocery store…I like grocery shopping. It’s a good thing because I like to eat. I haven’t always been so confident at checkout though. Back in the day, I avoided checkout lanes. I only processed my purchases through the self-check kiosks. So long as I didn’t screw anything up, I wouldn’t need to interface with anyone. Any doubt about me vanishes when I speak. I now decide which lane to go through based on what I have to check. Does it bother me if my voice gives me up? Not anymore! My voice is what it is, but I am self-conscious of it.

When I arrived at the grocery store, the parking lot was packed! After driving around, a spot came open at the far end of the lot. Considering the distance to the store, I contemplated changing into my flats. But thought no, by golly, I am going to wear heels. If you are going to get good at this thing we do, you must have determination and tenacity. Above all, self-confidence! So, off across the lot I walked…in heels.

Approaching the store front, I noticed people lining up for the cart attendant to bring them a cart. I took my place in line, enjoying listening to other people complain about the inconvenience of having to wait. I felt perfectly wonderful to be among them…even if they were complaining. It wasn’t me they were complaining about. I don’t think they even noticed me! After I received a cart, I made my way into the store and navigated through the crowd. I’m sure there were more people than safety protocol would recommend. The shelves were picked bare of several of the items on my list, which meant shopping at another store. It would also mean mingling more with shoppers; I didn’t mind. Being out-n-about among others builds confidence. I don’t recall seeing anyone else in heels.

As I approached the checkout, all the lanes, including self-check lanes, were backed-up. I chose the shortest line. It soon became obvious why it was the shortest. I was number four in line as the three in front of me had overflowing carts. Adding to each one’s frustration, the clerk was a young trainee…and slow. I didn’t mind. I stood there shuffling from one foot to the other…in my heels.

Shoppers continued to fall into line behind me. I listened to their conversations for mentions about the tall, female appearing person wearing heels. I felt a slight tug on my jacket and a voice behind me said, “Say, has anyone ever told you that you are tall?” Turning to speak to the person behind me, I had to look down. The owner of the voice, a lady, couldn’t have stood taller than five feet. She was adorable! Smiling, I replied, “Yes, I’ve been told that.” Then she said, “I bet you can reach items on the top shelf?” To which I said, “I can, but it’s the bottom shelf that’s a challenge.” As we chatted, she commented that there were too many people in the store, and she would have to return because the store sold out of a few items from her list. I agreed and said I couldn’t find items either and would stop at another store on my way home. She wished me luck and cautioned me to… “watch out for crazy drivers.” Chuckling. I wished her a Merry Christmas and turned back in line. I didn’t sense anything suspicious during our conversation. This thing we do is a self-conscious/awareness activity. So, it’s great to be able to “chat” with others. It relieves tensions and the anxiety of wondering what others may be thinking, or saying, about you. Interacting with others creates a warm feeling!

Finally… It’s my turn to go through the checkout. The cashier was young and personable. He asked the usual cashier questions. He did look at me several times with a queried look, as if he weren’t quite sure of something. I felt it had to be my appearance. That’s when you start to wonder if your blouse is gaping open, or your lipstick is smudged, or one of your earrings or nails is missing… A myriad of suspicious thoughts run through your mind. It compounds and you might even blush. When this happens, I’ve learned to ask a question, to distract the person from their perceptions. For them, I think it either confirms a suspicion, or casts enough doubt that they accept what they see. I think he accepted me as the female I appeared to be, because he said, “Merry Christmas!” and “we’ll see you again soon ma’am.” That is a compliment to hear!

By now my feet are feeling as though they have been cooped up long enough, especially one toe. On exiting the store, I stopped at the Salvation Army pot to deposit another dollar. When I got to the truck some jerk had parked so close that I had to position my cart behind the truck to unload it. It caused me to squeeze in sideways to get into my truck. When I got in, I looked down and saw a fella in the car playing with his phone. Geez! He could have offered to help the lady…Some people!

The parking lot at the next store was also overcrowded, but I was lucky to find a parking spot closer to the door. My feet ached and I wanted to change into flats. I didn’t want cramps tonight. Regardless, my goal was to complete the day in heels.

I entered the store, picked up the last hand basket, and made my way through all the congestion. I found all the items quickly but wanted to mingle amongst the crowd before checking out. I aimlessly walked up and down aisles, sometimes having to wait for an opening in the aisle to pass. I helped people reach items on the higher shelves, and was butt bumped twice followed by an “excuse me ma’am.” Both the bump and the apology felt wonderful! Incidental Interaction is a great way to meet people…which builds confidence.

The checkout lanes were congested here, too. I shifted from one foot to the other as I patiently waited in line. I felt a tap on my shoulder. I turned to face an elderly gentleman bundled up in his winter coat and cap, who was holding a small bag in each hand. He held up the two bags and said, “My chicken is getting cold.” I could sympathize with him. He asked what it was the cashier had put in the lady’s sack? I asked him to describe it. “It looked like little balls on a stick.” I suggested it might be Brussel Sprouts. He replied, “I didn’t know Brussel Sprouts grew on a stick.” And reiterated that his chicken is getting cold. My feet ached… I wanted the line to move along too. When I approached the cashier, she looked at me eye to eye and asked for my member number, along with the typical cashier questions. We chatted about the weather, and crowds, and on leaving she said, “See you soon, ma’am.” Oh, how wonderful to hear! There were no dubious looks or reactions during our conversation. I wished her a Merry Christmas! The Supervisor approached me as I exited the checkout lane and complimented me on my blouse and leather jacket. It was a wonderful interaction and experience…and feeling of joy.

When I returned to my truck, I rubbed my toe and changed into my flats. I am proud of myself for having gone all day in heels without experiencing any setbacks such as a twisted ankle. Even my voice didn’t seem to raise suspicion…And I’m so glad I brought my flats!

It was a day filled with wonderful experiences. My enjoyment comes from confidence. I derive that from the encouraging comments to photos and messages from CDH friends and members…and from mustering the courage to step out the door.

My wife and I have identified elements of my crossdressing needing improvement. Today, I focused on speaking and wearing heels. Kitten heels, but heels, nonetheless. I hope many of you can relate to my experiences. I wish that those of you who want to take that step out your door but are hesitant, enjoyed being with me vicariously in my adventures.

I acknowledge that June is a living force within me. As I envision who I want June to be; I continually work to present June with poise and confidence, and I accept that I am my own kind of beautiful!

Please join me on my next adventure…