Member-only story
As I entered my second gender transition from cross dresser to transgender woman I considered it as sliding down a very slippery gender slope. For years I was paranoid about how I would negotiate a landing. Or, how would the world and people close to me accept the reality of my gender transition.
Little did I know my paranoia would be wasted because of friends and most of my family accepted me with no problems.
The hole I dug happened before all of that. As I attempted more and more to explore the world as a transgender woman, I became increasingly brave in how I was attempting to accomplish my goal. An example was how I was able to leave the house cross dressed so many times. Seemingly without exposure. I did most of it from an 1860’s vintage brick house we were restoring. Since at one time in it’s past it was a boarding house, it had several doors I could use to sneak out. Many times in the very beginning I was able to go out and walk around the block. Before I moved up to being brave enough to take the car and drive around knowing full well I was risking a huge fight or even a divorce if my wife ever found out.
Still I worked hard to dig my gender hole deeper. I went as far as saving all the spare change I could find to augment my ever growing stash of clothing and makeup which I was able to hide in a spot she (my wife) never went. At one point of time I needed…
