This is actually a two part post combined into one because it involves a similar topic.
As I began to become more comfortable in going out on Halloween in feminine attire, I decided to try my good fortune by going to large so called straight venues. In my mind to do it correctly I had to go by myself without my wife.
The first time I tried it was with my first wife who was very vanilla and didn’t really seem to care. I often thought I could tell her I was going out for gender realignment surgery and she would not care. At any rate, as Halloween approached that year, I had already made up my mind I was going to the biggest venue in town as a woman and see what happened.
My “costume” was all in black with a tight sweater, mini skirt, black tights and blonde straight wig. All topped off with a black beret. The whole outfit worked well as people I thought I knew merely passed me off as another costumed Halloween person. However, all of it came to a halt when a person in a full mask stopped to see me and said he knew who I was. I was floored! How could anyone see through my elaborate “costume”? Finally I said how did he know me and he said I looked exactly like my Mother. It turns out he was a childhood friend who knew my Mom. Turned out later he was a notorious transphobe who made extremely derogatory comments about me behind my back. But that’s another story.
Other than him, the night I thought went well and I enjoyed myself immensely. What I was discovering though was how natural I felt when I dressed in feminine mode and interacted with the public.
The second part of this post deals with another experience I had when I was away from home training managers for a company I worked for. This one occurred with my second wife who also knew I cross dressed but was much more strict about my comings and goings.
Once I found out I was scheduled for a training seminar in a city I had to overnight in for a couple of days over Halloween, all I really had to do was figure out how to sneak a “costume” out of the house for the evening along with all my work clothes of course. With a little creative packing I was able to pack what I needed.
For the evening I basically had the same objective. Dress to blend with the other women at the venue in their Halloween costumes. I found a tight, short faux leather skirt and top, added fish nets, heels and heavy make up with a blond wig and off I went.
Much like the first night, all went well except for a few unwanted butt feel ups. All to quickly as I always say, it was back to being my same boring guy self. The only problem this time was I had to chase my gender euphoric fog in a hurry. The very next morning I had to teach a class at 8 AM. I made it time wise after triple checking I removed all the makeup from the night before.
While I certainly wasn’t the “belle” of either ball, I still had a great time!