First memories first. I remember watching TV as a second grader and seeing a celebrity boy dressed for a Christmas party in a velvet dress and thinking I would like to do that. On through high school there was the occasional use of female clothing accessible in the house and dreams of long flowing hair. Collage and girls moved these thought out of my mind. On to post grad education and marriage kept Ann at bay. Of to the army in Japan rather then RVN let some time for recreation and those geisha girls had really nice robes!
Back for five more years of post Doc. training and time for more of Ann though she still had no name. Dressing took the form of night clothes and under clothes. Three kids helped keep it under cover. My wife did not like it very much either. Trained at last , on to work twelve and eighteen our days relegated Ann to out of town trips. She went from under clothes to high heel shoes at night to drug store make up applied with no help. The web introduced me to a wider community and some instruction in “passing”. We were fortunate to acquire an apartment in NYC along the way and solo trips allowed me to get out in the city dressed. Early on I would get a hotel room for a night and change. I was not that passable but felt fabulous and used the response of the public to help alter my look. I found that most people hardly looked at me, and New Yorkers pride themselves in not reacting.
The next phase came with some instruction from Miss Vera (years ago), learning about corsets, and perfecting my look to the point that I could fly -pre picture ID- as Ann with no comment. I found Karen at her wig shop on 57th and got a natural looking hair do. Now I am the veteran of many trips as Ann, full time, for weeks at a time. I will never be perfectly passable but am treated by most as the person I am trying to present my self as. Each time I improve, My wife dose not approve but tolerates and very occasionally participates. I have lost out on some things and gained some things but as with most I had to make the trip on the path that was presented to me and for the most part it has been a very pleasant journey.