Life Turns on a Dime -Part Eight

I thought seriously about calling this post "The Slippery Slope." The time period covered is approximately 2007-2010 and is the time right after my wife passed away. Before we go any further, it is fair to note she somewhat supported my cross dressing desires but was dead set against any HRT or transgender moves.

Throughout my life I didn't have many male close friends and the three I did have about this time all passed away during the same time period. Plus I was coming ever closer to losing my business during the recession. So, I was left looking at a bleak social period in my life. To combat the abject loneliness I stepped up my visits to a couple of upscale sports bar/venues I was fast becoming a regular in.

During one of my visits, my regular bartender suggested I ought to meet her lesbian mother which turned out to be a friendship I have to this day. Then, on another night, another woman slid a note down the bar expressing her respect for me being me. I of course thanked her and another long term friendship was born.

Also during this time, I started to try several on line dating sites. Of which, most were dismal failures except the one I met Liz on around 2010-11. So slowly I was starting to rebuild my other life as a woman from the ashes of who I was. None of these people had ever seen or known me as a guy.

The slippery slope came as the three of them began to invite me to all their fun spots as the new me. Even a NFL Monday Night Football game! Finally I figured I had slid so far, these people had pushed me right off my gender cliff. Where is always where I wanted to go anyhow. I just didn't have the courage to do it.

Looking back now, the years were a whirlwind of learning. From learning the basics of using the women's room to dealing with men, almost all was new and exciting. There was one man in particular who treated me with respect and dignity (I enjoyed) among the rest who stood me up or expected me to dress them up. And then there was the experiences of going to lesbian mixers and being accepted (for the most part.) I went from being a "wing person" for one of my friends to being subjected to a giant/mean gender slur by a lesbian at another.

Undoubtedly, the most important part of falling off the cliff was the soft landing. Some of the padding was provided by my friends and other by my tough skin and willingness to learn. That is why I get so amused at those who think this transgender MtF transition process is so much fun or a walk in the park.

Coming up next, the doors open wide.

Thanks "Nat Geo"!

And thanks to all of you who have pointed out it's issue on gender which features a nine year old transgender girl on the cover.

The magazine has come along way and we need it as a respected counter balance to Brucelynn Jenner among others.

I think those of us of a "more mature" age still don't understand all the positive ramifications of a younger generation who see less gender in their world!

Regardless of what happens in the years ahead in Washington, some basics will never change such as when I went to Liz's company party the other night. Following the normal looks I get, everyone settled down and I had a great time and even met the wife of a fellow fledgling transgender person who is trying to find her way.

My only problems came when I was on the road all day and forgot to pack my backup makeup in my purse. I thought I could have presented better but then I always think that.

I would also like to thank Stana from Femulate who was kind enough to plug my book today. Stilettos on Thin Ice made it up to the top 6% of non fiction books on Amazon last week. And yes, book number two is still in the works.

Life Turns on a Dime - Part Seven

Time moved on and I found myself in the mid 1990's beginning one of the most difficult decades of my life for several different reasons.

To make many long stories short, during this time I was taking every possible opportunity to live my life as close to a woman as I could. Plus during this decade I was going to purge a year or so before my wife passed away. I grew a beard and ballooned to 275 pounds. Also, my Dad and three of my dearest friends were going to pass away and I was going to lose almost everything I worked so hard for during the recession.

Since I have jumped so far ahead, now let me back tract to a couple key events I have written about here in the blog during the past which gave me the courage to move on in the feminine world.

Since I became relatively secure in my abilities to negotiate the world in certain "safe" spots such as clothing and book stores, I felt it was time to spend an evening as close to being a woman as I could. Could I go stealth?

I chose an upscale restaurant bar for my trial because running a similar operation was what I did for a living. I knew once I made it past the hostesses, I would have a fairly easy trip to the bar where a group of professional women gathered after work for a drink most nights. I hoped if I dressed the part I could fit right in...sort of. That is if I could breathe because I was sooooo scared.

The five minutes or so I spent in the parking lot gathering my confidence seemed like five hours before I pulled up my big girl panties and went in. As suspected the hostess gave me the once over and asked if I needed a table and I said no "I was only there for a cocktail" and she directed me to the bar which had a couple big wooden posts on each end. Fortunately, there was a seat open near one, so I could do my "wood" impression blended in,  swept back my long blonde hair and ordered a drink. If indeed the bartender knew anything was amiss I don't know to this day but I was served, ordered another, tipped well and left. As I finally began to breathe again, I knew the night was something I wanted to do again and again.

The evening emboldened me to try to go to other similar places. Some of which I was successful and others not so much, mainly because of having to use the women's restroom. Along the way, I got kicked out of one place, had the cops called on me twice and got screamed at once. Through it all though I knew I had to keep on trying.

The biggest lesson I learned was I needed to adopt one similar style and stick with it. Or, quit being a blonde one night, redhead a couple nights later and a curly brunette a couple nights after that. In essence I was building an exterior image to fit my evolving interior.

Unfortunately, my extra curricular activities brought me more and more into possible contact with my wife.  One night after she caught me out again, we had yet another giant fight which led to me taking a whole bottle of one of my meds which luckily didn't kill me. I knew then the only way to stop the lying and sneaking around (which I considered cheating) was to grow a beard.

I'm proud at least I did because a year and half later she would be gone. Passing away from an unexpected heart attack after 25 years of marriage.

Coming up in the next series of "Dime" posts...what's next...or getting pushed down the slope.