Crossdressing: My Beginnings

When I reflect back on my early years of 'dressing up,'  there is not a great deal I can with recall with certainty.  What I do know is that one day I went to my sister's bedroom and tried on several of her dresses and outfits. I did so on a school day.  I had stayed home sick from school and I was alone in the house, a house normally filled with four siblings and two parents.  How old was I?  I cannot recall.

Regarding my age, I was older than eight and not yet thirteen.  I first visit her home in a house that became our home when I was eight.  When I was thirteen,  I can recall trying on one of my sister's sweaters and being frustrated that the pin in my thumb kept snagging.  What pin?  I had inadvertently stuck my hand into the blade of a table saw that school year.  I almost lost four fingers.  They were able to save my fingers with a pin protruding from the tip of two of them including the thumb for healing purposes.

This hand injury was the second of  two major health issues  I had during this time.  Two years before, at the age of eleven, I had appendicitis with complications.  After three weeks in the hospital and three surgeries, the doctors sent me home with the certainty that I had less than seventy hours to live.  But I bounced back and after another week back in the hospital and another surgery,  I was released with the doctor's assurance that all was better.  They must have been right because here I am still ticking.

I do not share these stories in search of pity or sympathy.   I share them because I lived in a small house among a big family and yet for several years no one ever 'discovered' that I dressed in first my sister's and then my mother's clothes.  Or did they?  As a parent facing the loss of your child in the weeks, months and years that followed would you not be willing to look the other way when it came to some of his pastime --     even if you disapproved.

In the weeks and months leading up to my first extended hospital stay and in for several weeks and months after, it was not uncommon of me to tell my mom I was in pain or not feeling well and she would allow me to stay home  -- unattended.  It was on one of these days that I made my first visit to my sister's room.  I will also share  that during both my appendicitis and my hand injury I was given a ton of pain killers and other medicines.  My life during these years is something of one big blur.  It is also relevant that at the age when most young boys are becoming young men, developing a love of sports and an interest in girls, I spent a great deal of  this time unable to be active in sports and socially separated fro the rest of my class including the girls.

We were on the stairs my younger brother and I one day going up to our bedroom when he confided in me that he had heard our parents scolding our older brother.  According to him, he had been caught wearing some of our sister's clothes.  It was a memorable moment for me because I had never consider wearing her clothes and yet hearing that my brother had dons so, it suddenly occur to me that I should give it a try.  Not to copy my brother.  But because it felt like an answer.  An answer?  What was the  question?    No real question, but rather the gnawing discomfort I felt that something was not right with me, that something was wrong, that I was not who I was meant to be.

Did I wait weeks or months before giving it a try?  As is so often the case for me, I cannot recall.  I do however know that it did take me quite some time to find both the opportunity to do so and the courage to do so before I would make that first visit.  Why coiurage?  As I have shared elsewhere, because I had the sense that it would answer my questions and answer them in a way that would prove me defective as a boy and sinful as a Christian not to mention most likely the only boy in the whole world who wanted to be a girl.

I have shared in a previous post about how my parents wanted me to be a girl.  I cannot also recall sitting on the bathroom counter and watching my grandmother put on makeup that made her so pretty.  And with just a bit of shame I must admit that my grandmother rarely closed her bedroom door, even when she was dressing for work.  Something about the clothes she wore enticed me.  Also, because we were a big family, because we were poor (my dad was a teacher at a rural high school), because Mom often had to work, and because Dad often got mad at Mom when the house work was not done,, I took it upon myself to do most of the household chores.  It was a commonly told family joke that I would make some woman a 'great wife' one day.  Finally, my Dad doted on my sister, gave her a greater share of his time and love.  I am not saying he loved her more, but he obviously cherished her more.  If I had been the daughter I was meant to be, I would have been the apple of his eye.  In short a therapist could have me in therapy for months with the fodder that was my childhood particularly when you add in that I started 'dressing up.'

So here is the wrap up.  On the day that my younger brother told me about my older brother, I know only one thing about how I was feeling about myself.  I felt that I was somehow different from other boys.  I did not think of myself as transgender.  It would be several years before I would ever hear that word.  Nor did I think of myself as a girl in a boy's body.  I simply felt different, different from other boys.  I will take that one step further and say that hearing about my older brother had we wondering if my life might not be better as a girl.  More consequential, I quickly jumped to the fantasy that it would be better as a girl,  From my first experience with 'dressing up' it was never about dressing to look like a girl, but rather dressing to be a girl.

As an young crossdresser I took a great deal of satisfaction from how well I successfully protected my secret  from my family.  And yet as I reflect back, I am forced to consider two possibilities.  One is that my parents never knew because I did such a great job as protecting my secret or they knew and simply chose to look the other way, not wanting to cause me any additional grief in my young life.  It seem much more likely that they knew.   They were not dumb and I truly doubt I was as sharp and as clever as  I thought I was.  Were they in their silence and indifference being supportive of a son that they already sensed would never be like other boys.

This is a glimpse of my story.  It is story I find compelling because it is so meaningful to my life.  I say glimpse because  I have so much more I could share.  What I have said so far is enough for the purpose of this blog post.  If I have accomplished nothing else, I have tried to convey that my decision to cross dress was the decision of a boy, a boy who felt different, a boy who did not like being different, but knew by being more of who he wanted to be, he was only making himself more different.  And with that, I will call that the end of my story.