TL;DR: I had a great experience riding Amtrak dressed.
Last week I had to work Monday-Friday in Washington, DC. I had decided to take Amtrak, as my client was near Union Station, and besides, riding trains is fun. As the date got nearer, I decided to "ride pretty".
My wife dropped me off at the station in my city of Durham, NC. I wasn't checking bags, so it was just a matter of getting on the train with my rolling bag and my backpack. I was wearing a black denim skirt that came just below the knee with a bright pink sweater, My outfit was completed with gold (fake) hoop earrings and a gold necklace, plus black tights and black leather flats. My wife lent me a cute multicolored scarf that went well with my pink sweater.
I had an incident that in the past would have caused me to DIE with embarrassment when I first got on. When I reached up to put my rolling bag on the overhead luggage shelf, my skirt fell down to my knees. I just quickly pulled it back up got into my seat. There were people around, but no-one laughed or said anything. (When I got to the destination, I was careful to lean against a seat so it didn't happen again).
I had a window seat in business class, and for the first part of the trip, no one was sitting in the seat next to me. I went to the snack car a couple of times, and really didn't even get any funny looks. The credit card reader was a little complicated, and when it was my turn to pay on one of my visits, I repeated the instructions that the snack bar guy had given the two previous customers. He said "You actually listened" :-). Then, the gentleman of an older couple behind me (late 70s or early 80s, I'd guess) said "This lady will show me how to use my credit card", meaning me. I did, of course, and it made my day. I got "ma'am"ed by a conductor.
When I got to Union Station in Washington, I got a cab to the hotel, since I wasn't sure how the walk was. Cabbie and I made small talk, then I checked into the hotel. After freshening up a bit, I walked to a fast-food Korean place near the hotel for dinner.
I finished my work around 3:30 on Friday, so I went back to the hotel got shaved, cleaned up, put on makeup, etc. I dressed in a flowy mid-calf skirt and a dark blue long-sleeved top, again with black tights and my black flats. (I couldn't bring a lot of women's clothes since I needed 5 days' worth of work clothes as well. I walked to the King St. Oyster House, a few blocks from the hotel, where I had a nice dinner and chatted with a woman who was having dinner next to me with her male companion.
Then I walked to a Metro station and took the Metro to the Dupont Circle station. I went to a late-night place that my wife used to go in the 80s, when we lived in DC. I took the Metro home and had no issues the whole evening. There were some 20-something guys on the Metro, and one got up and offered me his seat. I told him I was fine, but it was a sweet offer.
Saturday AM I got up and got ready, wearing the same flowy skirt, but with a ribbed cotton sweater and a chunky necklace. I walked to Union Station (about 25 minutes), and got there about an hour or more before my train, so I got a latte and a scone. The seating area for the coffee shop was full, so I asked a young women if I could share her table, and she was fine with it.
This time I checked my larger bag, and then went to the waiting area. I used the very busy ladies' room. I boarded the train without any problems, and had an uneventful trip home. The train got to Durham about an hour late, and my daughter and non-binary grandkid picked me up.
The trip went so well that I think I would now consider flying pretty, which had always been a little scary before.
All in all, It was a crossdresser's fantasy trip, and I am grateful I was able to do it. I ticked off several bucket-list-type items: train travel, Metro, nice restaurant solo. Oh, the work went well, too.
, Looks like you blended in Perfectly.
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