Saturday, February 26, 2022

Crossing the Cross Dresser

 Recently I think it was Mark who was confused by a few of my comments about me transitioning from a cross dresser all the way to a full time out (and proud) transgender woman.  Finally, I got it through my thick noggin not all people understand what I am writing about.

Over the years too, I have tried not to be condescending to all cross dressers by appearing to take a "transer than thou" attitude. Most of the time I tried to add a sentence alluding to the fact, in many ways I spent nearly a half a century trying to decide or gather the courage to face head on my reality...I was always destined to live in a feminine world. Completely. 

Finally I came to the conclusion my life was a series of gender transitions. From innocent explorer into my Mom's clothes to a full fledged exploration of girl's fashion all the way to hormone replacement therapy and living full time as my authentic self. All of them sandwiched in between life's normal transitions as we age.

If I had been true to myself I would have understood years ago I was more into being a girl than I was looking like one.

As I wrote in a recent post, there are very few people who knew me at all in my cross dressing days and Connie was one. Here is her comment:

Cross Dressing Photo
JJ Hart

"I guess, technically, I met you (online) when you were still considering yourself to be a cross dresser. I remember expressing my doubt to you when you told me you were content balancing your male and female lives. Of course, I never knew the "before you," even if you were showing that to others. It didn't feel to me as though your transition was anything other than inevitable - even as hard as you were trying to make a cross dresser's life work. I knew it because I had realized it of myself. I think that I even asked you if you thought you were cross dressing as a female or a male. ;-)"

Thanks for the insightful comment. Again it wasn't until I started to live as my authentic gender self, did I realize I was viewing life the entirely wrong way. All those years I was pretending  to be a macho man, all I was doing was cross dressing as a man.

So, as you can tell, I believe there are many levels of cross dressing to consider and the bottom line is if you feel good doing it you should.

Life is too short to go at it any other way.  Only you can determine how supposedly selfish it is to involve your gender pursuits with others. I have been amazed over the years how some cross dressers either are able to stay in the closet. In many ways they could be a better person than I. Straddling both sides of the binary gender spectrum nearly killed me.

Crossing the cross dresser was the only way I could go.


  1. Well, you can't say I didn't warn you. ;-)

    For me, I could no longer live with the stress of attempting to live two separate lives. I hated the person I had become, with all of the lying, deception, and denial that it required. My life as a cross dresser was really no life at all. The relief from my depression was only tempered by the act of cross dressing, and it was but a vicious circle of meaningless events, divided by guilt and shame.

    What I finally came to accept (long after my realization) was that I could only be true to myself through my honesty with others. While I had thought that keeping the trans-me a secret was protecting those whom I loved, I was only causing them the pain of living with an unhappy and terrible person. Looking back on it, I had nothing to lose, because I was on the precipice of losing everything and everybody, anyway. I had designed it that way, out of my own weakness and fear as the terrible person I had become.

    I can't say that I envy those who can live a cross dresser's life. I've heard some say that they are bi-gender, and maybe they are. For me, that would be a rationalization. I am definitely a binary trans woman, and living any other way would be a compromise for me.

  2. Towards the end of my days cross dressing (or before I worked out who I really am depending on your point of view) I found it increasingly difficult to maintain the lies and secrecy, added to that was the string feelings of bereavement every time I packed "her" away.

    During this period I started to "leak" ~ that is I would hold onto feminine items around my male persona, female jeans, female ankle boots, tee shirts or sweaters. On at least one occasion I forgot to remove ma nail polish! It has always amazed me that only one person worked it out before I came out.

    Linking in to the whole "you're so brave" thing I think I just gave in to the inevitable. As Connie says it's not just me that's happier now, everyone I impact on is as well.