Halloween has always held a special interest for me–and for many fellow travelers.
In grade school, I was envious of the boys who got to dress as girls for Halloween.
Sixty years later (give or take), I still am.
About ten years ago, before I was going out regularly, I had some brief Halloween forays out. A few hours dressed, walking around a popular St. Louis neighborhood, and another year brave enough to walk into a Dress Barn (RIP).
Maybe half the years since I started going out regularly in October 2016, I’ve been traveling somewhere, but I’ve tried to go out on Halloween when I’ve been able to. These days, usually the only issue is what I’m going to do, and when I tell my wife. This year, my GG BFF Michelle and I had decided to go out together, and she was going to wear my Wonder Woman dress. I told my wife about a week before, and she was OK with my going out.
As Michelle was wearing my dress, I decided to turn the tables on her. A few weeks before, I saw a Facebook picture of her in a costume she wore to a 50th Anniversary showing of The Rocky Horror Picture Show at the Fox Theater. It looked cute and suitable for Halloween, and I assumed if it fit her it would fit me, and it did (it is fun to be able to wear a lot of the same clothes as a GG who is freakin’ gorgeous).
As Michelle got off work at 2:00 p.m. on Halloween, we agreed to meet at her house at 2:30. For once, I was early (becoming a girl for me usually takes longer than I expect, but this once I managed to make it happen on time). I wore a blue American Eagle summer dress I bought at a deep discount about a week before. I also brought to her house the strapless blue top and skort combination I bought during Dee-Va Las Vegas, so I could model it for Michelle.
After a short errand together, we returned to her house, and her boyfriend had arrived from his work. We drove to a local barbecue restaurant for a late lunch, then returned to Michelle’s house to don our Halloween outfits.
Michelle had acquired additional Wonder Woman accessories, to make it a more complete outfit than just the dress. I put on the costume that she had shared with me, while her boyfriend became Clark Kent changing to Superman (his was the easiest of the three to accomplish).
After getting ready we went outside and took some more pictures including shots of Michelle with Zee-Zee, her Ford Bronco. After pictures, we drove to her friend Maura’s house. Maura (the costume I was wearing was actually hers) and her husband had invited us over for their Halloween festivities. We had a drink ate some food, and saw a few trick-or-treaters. Maura complimented me on my look, and we finally we left for our destination before I ate too many chocolate bars.
A few days before Halloween I discovered a burlesque show in downtown St. Louis, and suggested it to Michelle, and she was all-in. We arrived, took some more photos in the bar area (have I reminded you Michelle was once a model?), and then were seated for dinner and the show in the main auditorium.
The dinner was pretty good. The place was perhaps two-thirds full, with about half of the guests in costumes. The show maybe was a B+, although one of the performers did amazing acrobatics on a pole. This show was a little tamer than the burlesque show had been to earlier in the year, but this was a more suitable viewing environment. We had a nice time and enjoyed the show, and I enjoyed celebrating the National Crossdressers Holiday.
