By Dee
Before I started going out in public, I read blogs and forum posts about traveling while crossdressed. One such blog was (and is) titled “Traveling Transgendered”. The author (Kimberly) wrote about her travels (usually for her job, with bulky tools in tow), and I eagerly read about her trips. Kimberly also coined the phrase “Flying Pretty”.
Once I started going out (which I wrote about previously in Kandi’s Land), I wanted to challenge myself and take a trip out of town. My planned destination was Chicago. I live in downstate Illinois, so Chicago was a suitable choice. I wasn’t confident enough to handle flying pretty (and I’m still not ready to do it, two plus years later). Driving meant dealing with restrooms along the way, plus the expense of parking in downtown Chicago, so I chose the train. Instead of “Flying Pretty”, I was “Training Pretty”.
These events all happened in early April, 2017, roughly six months after I started going out. It’s a 6 hour train ride, leaving from downtown St. Louis a little before 8 AM.. As it takes a LOT longer for the girl me to get ready, I was up at 5:20 to shower and shave (face, arms, legs), eat breakfast, do my makeup, dress, finish packing. I drove to the local Metrolink light rail station (fortunately, this was Sunday morning, so the train was mostly empty), and took the Metrolink to the St. Louis Amtrak station. The train was more full than I anticipated. I was also dressed more formally than most; I decided if I was doing this, I was doing it in a dress.
I wanted my nails done for the trip, so the afternoon before I went in boy mode to get my manicure. I returned to the same salon I had gone to the prior October, hoping to get the same nail tech I had then (who was great and extremely supportive) but she wasn’t working.
Instead, in a stroke of extreme good fortune, the tech was Michelle, who possesses a pronounced Southern accent (by way of Arkansas). I told her I wanted girl nails and showed her the polish I wanted (I had brought it with me). She could have not been more excited. I showed her pictures from my phone and she gushed about them. Michelle told me I could have come in dressed, but I told her didn’t have the time to get ready. I told her that I was planning to dress on Thursday morning, and as she and she was working Thursday morning, I said I would stop in (if someone wants to see me dressed, who am I to say no?).
The train arrived in Chicago around 2 PM. I walked to my downtown hotel (about a mile), and checked in. I had never done this before in girl mode. But check in was painless. They wanted photo ID, so I handed the clerk my driver’s license and said “I’m hiding in here somewhere.” [Editorial comment: I may have to use that line myself!]
I went to my room, hung my dresses, and changed into my stealth (casual), clothes, a top and and skinny jeans. Off I went to find some lunch and hit some shops (fortunately, downtown Chicago is chock full of prime retail therapy opportunities). Did some looking, and then found a sports bar to watch opening night of the baseball season (Cardinals versus Cubs, which is the big rivalry, and was the first game after the Cubs won the 2016 World Series). After the game, I returned to my hotel, mentally ready for day two.
Tune in next Sunday for more…..
from Kandi's Land https://kandis328772669.wordpress.com/2020/01/12/training-pretty-day-one/
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