The Toughest Night

Recently I was asked to submit a few answers and experiences from my transgender past to an aquaintance of mine who is writing a book.
The toughest question to answer was the experience of mine which was the most difficult. As with most transgender folks I had plenty of those to sort through in my mind. Finally here is the one which really stood out:


" I thought back to the first time I went out as me to a Fridays approx 15 years ago. I had quite a bit of experience in gay venues but my time in them just never felt right. As it turned out my wife was working that night until midnight so out I went. My "hair" of choice then was a long honey blond wig and I went with a very respectable pair of flats, slacks and a nice blouse. The Friday's was in an upscale mall area and I wanted to blend in well with the professional women who came in by themselves after work. The old picture above is very close to my look that night.

Before I went in, I sat in my car for what seemed like an eternity but in reality was probably 5 min or so. Finally I hitched up my big girl panties, checked my make up in the mirror and thought I had come too far to go back and went in. The hostess stand was an easier process than I imagined. I side stepped a family waiting for a table and headed for a seat at the bar while the hostess was seating someone else. The bar actually had two posts on the front two corners and one even had an open seat beside it. (I remember quite clearly wanting to become one with that post and essentially disappear.) Surprisingly though I had come this far and could still breathe plus no one had pointed, laughed or ridiculed me...Wow maybe I could do this woman thing!

Then, a very friendly bartender arrived and in my softest frightened voice I ordered a draft beer. At that point I was trying to breathe normally and enjoy the moment. I played with my hair, checked my blouse and curiously felt my panty hosed feet in my flats. I quickly drank two beers and left with a huge sense of accomplishment but little or no enjoyment. As it turned out the bartender who waited on me that night ended up at that Friday's for a decade. I went back many times and always appreciated the smile and a name greeting which normally always paved the way for a smoother reception at the bar.

As we all know most all of this process has really difficult moments but that night was a real life changer for me! Believe me, I have had my share of downright embarrassing moments which hopefully someday will totally just fade away!