After countless times dressing up/putting on makeup in the privacy of my own place, I stepped out for the first time fully dressed and in full makeup!
I was in the middle of one of my usual sessions, where I would put on my face and wig, and then try on some combinations of the few outfits I have, and lounge around dressed up.
It was pouring rain out and the TV news was warning about storms coming through. It was pretty bad out. And a little later, just as I was finishing my makeup, the rain suddenly slowed to a drizzle. Either it was inspiration or my femme self pushing me, but I realized that almost no one would be out, it was night, and I could carry an open umbrella to half-cover my face if needed. It was a chance to finally go out, passable or not, no matter!
I hurriedly selected something discreet and muted, and so I went with a grey women's top over a beige dress, with black tights. I also had on a push-up bra with molded cups that really help my man-boobs become more lady-like. And for me, the piece de resistance were some grey suede ankle boots with a heel. I settled my wig and brushed it down a bit, got my phone and keys in a little handbag-like satchel, and did a final mirror check.
I knew it was going to be in the dark with few people around, but I was still concerned about my hairy arms (I don't shave below the neck at all yet, something to think about later). So despite it being summer I put on a light grey long sleeved shirt under the top. The two pictures I attached show with and without that shirt just before I stepped out.
I stepped outside, and it was quiet as I had expected, with only a slight drizzle. I opened my umbrella, keeping it low, and off I went. I had no goal in mind, so I thought I would just take a walk around the block, then decide on anything else from there.
It was funny, being dressed outside felt a lot like being dressed inside (duh!) The biggest issue was the 5-inch heels!
(EDIT: I didn't have a ruler at hand and I eyeballed the shoes, but after checking online with other shoes and comparing, they are probably closer to 4 inches actually)
I had never walked in them more than back in forth in my living room, and now walking down the slightly rough sidewalk was totally different. It seemed if I walked too flat-footed, the heel would scrape and ever so slightly flex the heel area. It felt like I was "doing it wrong", plus I didn't want to ruin my expensive shoes, so I soon found myself walking more as if I were on my tip-toes, and after making contact with the toe area, I would lightly settle back onto the heel part. I stumbled once and made a wild swing with my arms as I caught my balance. In any case, I didn't feel very lady-like as I got used to doing actual walking in heels.
For a while I just tried to visualize how I would look to others, with my awkward walk and rather masculine build. Fortunately, there was no incident or problem. I passed one couple deep in conversation who didn't even look my way. Apart from the rain and, it was still rather hot and humid, and I felt a bit of sweat building up. Once I made a circuit of the block and was approaching my door, I figured with the extra shirt I had put on I was getting too hot, and there was no need to sweat all over my clothes at this point. So I headed back inside, and my first journey outside came to an end.
The one thing I would like to ask others regarding this experience is, is there a certain way to walk in heels that's "best"? I felt like I had to walk toe-then-heel so as not to drag the heel part on the rough sidewalk, but what does that do to my gait? Does it look really strange to a third-person observer?
Also, does anyone have some general walking tips for when in heels? My first concern is to have a natural gait and a "feminine" walk.
Overall, it was a great experience, the most notable thing being how relaxed I felt given it was my first time. I guess months and months of dressing up in private prepared me to be a little more at ease than I thought I would be. I'm really looking forward to the fall, where I can stay out longer without worrying about the heat. For now I'm going to aim for quiet evenings for stepping out, but who knows?
Ten Years Living 24/7 as a Mature Lady
