I recently had the opportunity to visit Orlando, Florida as part of a working convention which had nothing to do with crossdressing. Not being one to let well enough alone, or to miss a chance to dress on someone else's budget, I took along a few well chosen things, just in case.
The first challenge came in Houston, at the airport. There was a plane change, and Continental uses two different concourses. Normally, this is not a problem, but in a green, Pendleton skirt suit, with three inch heels and dragging along some luggage, it does present a moment of excitement. Alas, all went quite smoothly, although I did not look behind me to see if I had left my usual trail of destruction. Oh, well, at least the people at Continental have learned to deal with me.
In Orlando, I only had one night free to play. I decided to start simple, and went to the "Mystery Dinner" at the hotel where I was staying. This turned out to be a lot of fun. I selected a creme jacket with a satin shell underneath. A long flowing chiffon skirt in the same color plus creme shoes and a matching purse completed the outfit. (I may not have great taste, but my personal shopper at Nordstrom's certainly does.) Gold accessories and a bow in the hair of course.
Thus tricked out, I approached the reservation center. The staff groups all the guests together in the lounge first, so they can sort out the seating. Of course, at six feet one inch tall, plus three inch heels and an upswept hairdo, I am slightly noticeable in a crowd. Taking advantage of all the attention, I struck up conversations with several other guests.
During dinner, I wound up seated with what turned out to be a member of the cast. As the dinner progressed, and the murders increased, he became a prime suspect. Thanks to a line of dialogue accusing another unsuspecting member of the audience of being a secret cross dresser (thus seeming to plant a hint my direction), so did I.
People began coming over and talking to me, asking me all sorts of questions about my background, how long I had known my dinner companion, etc. The attention was delightful. I gave each of them a different answer, sometimes misleading them deliberately.
By the end of the evening, the audience was supposed to solve the crime. They were to select whom they thought had committed the murders. Despite several protestations on my part, I collected about a dozen people who were absolutely certain I was the villainess.
The cast got such a kick out of this that they invited me to stay after for a cast picture. This turned out to be a great way to start the evening, so I decided to press my luck.
Nearby was the Disney World nightclub center known as Pleasure Island. A short cab ride and I was loose in my own version of Fantasy land. The theme was Mardi Gras, and as I walked towards the entrance, the parade (featuring Caesar's Crew from New Orleans was just forming up. I walked along with the last float, talking to Caesar and admiring all the feathers on the float.
At the gate, the guard asked for my admission, and Caesar said, "She's with us!" They let me in for free. Of course, I did have to preen a bit for the parade watchers, but such is the price of fame.
I stopped at a club which featured jazz. I knew the band from earlier trips to Sacramento and Chicago, and wound up with the best table in the house, plus the band leader before the show. He left to get ready, and pretty soon, three gentlemen asked if they could join me.
One of them turned out to be from Seattle, my home, and was in a business similar to mine. We had a great conversation, and I don't think he figured out who I really am. At least, he has never mentioned anything.
We enjoyed the show, and when the bill arrived, the gentlemen bought all my drinks. So there you go. If you want to go out -- go. Don't be shy. What could be more fun than meeting nice people, becoming part of the show, getting free admission and free drinks all night?
Silly question! Doing it all again, of course, but that will have to wait for another trip.