I ended up having a need to take a short trip across country. I decided to bring some pretty clothes along. My wife asked me, "Are you planning on dressing?" I told her I was. She is not very comfortable with my dressing, but she is willing to talk about it some.
The busy men's room
As I flew out of my home city, I was dressed in drab. In my carry-on bag, I had my pretty outfit. When I got to the airport where my connecting flight was, I changed into my pretty clothes in the men's room. I put on a black and white, striped maxi skirt, a bright orange lightweight blouse, and a black cardigan. I never wear a bra or makeup or a wig. The men's room was rather busy, but I was mostly comfortable. I walked out of the stall and washed my hands in the sink with men all around me. No one behaved any differently toward me than if I were dressed masculine. Maybe the crowd helped.
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Walking the airport concourse
I had a long layover. I went to the gate for my flight. The concourse was mostly deserted. The only people there were like me, people with a long layover. I walked the whole concourse looking for something to do with my time and also for a place to eat lunch. I felt like a lot of people looked at me. I was particularly self conscious. That probably made me more aware of glances. However, I was not very stressed. I know that because I did not sweat heavily.
Compliments
While passing the time, I went into a store. An employee said, "That's a pretty dress." Some airline workers told me I looked fine when I drummed up a conversation and confessed how I sometimes feel awkward when dressed. I became less nervous. As I walked in the concourse, I saw a woman walking in my direction. As she approached, she suddenly smiled and said something kind about my skirt. It might have been, "I like your skirt" or "Nice skirt." I could not hear her well. This was a nice way to start my dressing outing.
I walked to the other end of the concourse. It was busy. It took more nerve. Some people did not pay me any attention. Some did not pay me much attention, other groups of people who were sitting down would suddenly all turn and look my way.
I eventually made my way back to my gate and sat down. There were only about a dozen people scattered around the many seats. Only a few appeared to notice me. Those who noticed me seemed to go on about their business soon after noticing me. I sat and read a book. About twenty minutes later, I got bored and decided it was late enough to go eat lunch. I walked down the mostly deserted concourse to a restaurant I had chosen earlier.
Chatting with a stranger at a restaurant
At the restaurant, I ordered my food and found a seat. I did not hide in the back. I sat near an entrance and even started talking to a nearby female customer. We talked for fifteen minutes. Eventually, I walked back to my gate. I had grown very comfortable. I had stopped looking in everyones faces. If they looked at me or not, I did not bother to find out.
When I returned to my gate, there were a lot more people there. I returned to my previous seat. There was a man straight across from me using his phone. He lifted his phone up as though to photograph me. I moved and he followed me with his camera. If he took my picture, I may have had a very angry face . I got up and walked to a seat where he could not photograph me. I started reading a book. At one point, a young man across the aisle to my left started talking to me about my book. We chatted for 20 minutes. After he left, I spoke to the big, muscular man across from me. We had been on the same first flight. He talked comfortably with me for five minutes until we got up to go board our plane.
Two CD/TG airline employees?
On the plane, I sat next to a professional woman. We talked, but nothing interesting happened with her. While our plane was still at the gate, I saw a woman come onto the plane to give the attendant something. She was a tall, large framed woman. She had on a wig. Around her neck, she had a stretchy band right where an Adam's apple would be. I think she was a transgender woman. She was dressed in her airline uniform dress and reasonable heels. She turned and left the plane a moment later.
After my flight, on my way to the baggage claim area, I noticed that someone was walking behind me. After the moving walkway, the person came along side of me. We looked at each other. It was an airline employee in a shirt and pants uniform, long black hair, feminine flats, black hose, red finger nails, breasts, but apparently a man. No make up. I spoke and he responded with masculine voice. No further conversation. I do not know if this person identifies as a a transgender person or as a man like me who dresses feminine and stays masculine. Later, at the baggage claim area, I saw this person waiting with a woman and a child.
Police officer and a rental car facility
When I got to the conveyor for my flight's baggage, I saw the big, muscular guy from earlier. We started talking. It turns out, he is a police officer. We talked for a long time while standing there waiting for our luggage. He seemed comfortable talking to me and did not seem to mind that it was just the two of us standing there for a long time.
Next, I walked to the rental car shuttle, and rode it to the rental car facility. I did my business at the counter and walked out. I went to my car. An older couple were getting into the next car. They took the time to watch me walk around my car and look for damage. It was awkward walking around my car while they sat and watched me. Then, she had her husband get out of their car and walk around it inspecting it for damage. She did not make him put on a skirt, though.
Busy store and someone laughed outloud
I drove toward my destination. I stopped at big store to get a couple things I wanted. There were long lines at registers. I got into one line for a while and then remembered something else I wanted. As I walked along, I heard laughing. There was a teenage girl with her mother. The girl was laughing at me uncontrollably. That was the worst thing that happened on my trip. I found what else I needed and then got back into line. I used the self checkout (because of the crowds) and left. Later, I stopped in a fast food restaurant for an early supper. I got it to go.
I drove on, and stopped at a couple other stores. At one store, I asked an employee to take my picture (above). She politely helped me and even took another set when the first set was blurry. She suggested a better backdrop. She was completely comfortable. I think I was too. Then, I changed and went the rest of my way to my destination dressed in men's clothes.
Return flight
On the day of my return flight, I put on an orange maxi skirt, my black flats, and a black and gray top with 3/4 sleeves. I made no stops on my way to the airport. I drove my car to the rental car facility. The girl who received my car was bright and friendly. She was professional and efficient. I went to the shuttle bus and got on. I was the only person on the shuttle bus. He dropped me off at the airport and I checked in at my airline. Some people looked as I went along, but by this point, I was not that concerned with it.
Searched in security
There was a corral at security, no problem. I was double-checked in security. No big deal. I hurried to my plane and may have been the last one to board. On my flight, I sat by a doctor. We talked the whole time. He was completely comfortable being friendly with a man in a skirt.
At the next airport, I planned on changing back into menswear. I realized that I forgot to get a picture of me in my pretty outfit. I asked a worker if she would take my picture and she did. Then I changed and went to my gate to catch my flight home.
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I am sorry this picture is so blurry. There was a bit of a language barrier between the nice lady who took this picture and myself. I decided it would have to be sufficient.