AMA #2 -- First Time Out In Public

Ask Me Anything #2

When you first went out, was it fully dressed or did you add more over time?

I don't remember the exact date of the first time I went out in public. I think it was sometime during 1991 or 1992. It was an exciting time for me as I had recently met several local crossdressers. For the first time in my life, I was sharing my crossdressing with someone other than my wife. I learned that there were regular monthly local meetings open for anyone CD, TG, or TS. I attended the first several meetings in drab (dressed as a boy).

Even though my wife knew about my crossdressing, there was no way I could change for any of the meetings we had young children at home. Fortunately, one of the crossdressers I had met said that I could change at his house. He went out quite regularly in public sometimes accompanied by his wife. He told me that he and his wife were going out to dinner before the next meeting and I should join them.

I don't remember too much about that night. I was so excited it seemed like there were gallons of adrenaline flow around inside of me.

Of course, I wanted to "pass" if possible. And if I couldn't, I didn't want to embarrass my friend and his wife. I decided on the "professional businesswoman" look for my first excursion in public. The first women's suit I bought had a black skirt, pants, and blazer. I think I bought it from Lane Bryant. When I first started thinking about possibly going out in public, I was worried that it would be difficult to find any women's clothes that would fit me. I had taken my measurements and checked the sizing in the LB catalog. It looked like they had something that would fit me! I quickly wrote up my order and mailed it in with a check. These were the days before the Internet and on-line shopping. Everything was done by mail. When I received my order and tried it on, I was very happy because it fit me perfectly! For my first excursion in public, this was the outfit I wore.  Here is a photo of me taken about the time of my first public outing.

Ready to go!

I actually have kept the outfit I wore that evening. I decided to try it on several days ago to see how I looked. The style and cut of the suit is from the 90's but didn't look too bad. Bowtie blouses are making a comeback.

The Professional Businesswoman

Looking back on my first time going out in public, I did not feel like a man in a dress. I felt very much like a woman. I wanted to appear as a professional businesswoman and I think achieved that goal. I remember my friend's wife telling me that she was surprised at how comfortable I looked and how easily I moved and acted as a woman. In other words, my movement and actions would signal to everyone that I was a woman out to dinner with friends. I truly FELT like a woman going out to dinner. Going out that night was made extra special because the people at the restaurant treated me like a woman.

I don’t remember too much about the dinner or going to the meeting afterwards. The evening was over too quickly.

I have been out in public many times since then. I never had to "add more". I always dressed appropriately for the event or outing. I try to blend in as much as possible. I've never received any bad or rude comments.

My first time out in public as a woman was a watershed moment for me. However, it caused a lot of problems for my marriage. My wife was adamant that I wouldn't go out in public dressed as a woman to which I agreed to in order to keep the peace between us. Instead of working through the problems I was causing, I decided not to tell her anything. Sadly, I became an excellent liar, something I am not very proud of...