Crossdressing -- When, How and Why I Got Started

There is a great deal of discussion as to whether or not if one is transgender it is due to genetic destiny or flawed nurturing. While I cannot discount the likelihood that genetic predisposes us to favor a feminine over a masculine self-image and no doubt genetics affects our personal appearance, personality and manner, I tend to see crossdressing and being transgender as more a product of one's upbringing.

I based this conclusion on a shared trait of all who crossdress and all who are transgender (using 'all' very loosely as there are always exceptions).  We all begin our journey by adopting the social role of our preferred gender.  At three, six and nine, a child does not know enough about being male or female to see this as a choice, but they have learned a great deal about being a boy or being a girl.

There Is No Single Reason We Become Who We Are

I feel it is important to know that being transgender or becoming a crossdresser most likely does not have a single explanation, a singular cause.  There is no better testament to this conclusion then that gender identity does not determine sexual preference.  I will also acknowledge that my thoughts on why one is transgender or why one loves crossdressing has been largely shaped by my own experience.

Before I discuss the origins of who I am today, I would like to stress that as a child, I was grappling for answers.  I had feelings I could not explain.  I was full of doubt and questions.   I found answers to my desires through crossdressing.  As an adult, I am no longer powerless to my urges.  I crossdress now because I chose to crossdress.  Am I transgender?  Is that why I crossdress?  Crossdressing allows me to dress as a woman in our society dresses, but clothes are not me.   While I do see myself as transgender (self-defined), crossdressing is supportive of that idenity and not what defines me as transgender.

Whether or not one agree with my position, whether or not one understands my position, is not of any concern to me.  At 53, I am who I am and I am who I choose to be.

My Parents Wanted Me To Be A Daughter

I am going to begin the question of why I choose to first visit my sister's bedroom one day at the age of ten by suggesting something rather bold.  There is one and only one reason I became a crossdresser.  I do not offer this as a factual statement, merely as a starting point for my discussion.  If it were a fact, what would be the single reason behind my life as a crossdresser.

My dad was an only child and when Dad married Mom they both knew he wanted a big family and he wanted a daughter.  There first child was a coin toss.  When they did not have a daughter, when Mom became pregnant with a second child, they wanted that child to be a girl.  That child was me.  I was born a boy.  It had always been their plan to have a large family so they had another child.  Having had two sons already, they did not have much hope their third would be a girl.  They had another boy.  Their fourth child however was born a girl. As the story was often told, if Cheri had been a boy they would have stopped at four sons.  As she was a daughter and they had three sons, they opted to have one more child in the hope of a three-two balance.  Instead they had a son and a four-one balance.

This story was often told when family and friends made comments to my parents about having four sons to raise.  I heard it told over and over and over  again going back into the most distant corners of my memory.  It is also fair to suggest that I heard it often told in those years into which my memory no longer travels.  There was however one aspect of this story that I glossed over in the previous paragraph.  Each time it was told, I was the focus of the story.  I was the son who was suppose to be a daughter, the boy who they wanted to be a girl.  While they hoped my two younger brother and to a much less extent my older brother would be a daughter, I was  the only one of their sons to which it could be said, 'We really wanted him to be a girl."  "Fred (my dad) had high hopes that Glen would be a girl."  "Glen was suppose to be a girl."

Did I Choose To Be A Boy?

As a boy of two or four or six, what did I know about being a girl.  I knew girls wore dresses and grew up to be Mommy.  About boys, I knew that they wore pants and grew up to be Daddy.  Each time I heard this story told, I had to sense their disappointment that  I had not been born a girl.  Or, . . .  And this is a question I might have had -- Did I choose to be a boy when Mom and Dad wanted me to choose to be a girl?  Did I choose to be a boy by dressing as a boy instead of being a girl by dressing as a girl?  Did it ever occur to me that Mom and Dad would have been happier if I had been born a girl?  Did it ever occur to me that Mom and Dad might love me more if I had been born a girl (which is not to say they did not love me with every ounce of their fiber)?  Did it occur to me to ask if I could still be a girl?

I am not suggesting that as a child of five that I sat down and pondered these questions.  What I am saying is that a few years later, when the idea of dressing in my sister's clothes was presented to me, it felt right to consider the option even as it by then felt wrong to actually do so.  So here is the logic.  At five, I hear my parents share that they really wanted me to be a girl.  At ten, I begin crossdressing.  Is it logical to see this as cause and effect.  I think so.  At the very least, it seem illogical to suggest that it did not impact my lifestyle choices.

The Seed of an Idea is Planted

One day I was hanging out with my younger brother when he mentioned that our older brother had been caught wearing some of our sister's clothes and had been scolded.  My brother shared this as a means of mocking our older brother, but upon hearing of this, an idea was born.  As mentioned above, I was by this tine old enough to know that dressing as a girl would only get me in trouble with my parents or ridicule from my brother and friends.  And yet it struck me instantly as the prefect solution to deal with some of my feelings.

It would be several weeks, maybe even a few months, before I would find both the courage and the opportunity to visit my sister's room and try on some of her clothes.  I did it one day when I stayed home sick from school, a day both of my parents were working.  (It was a different time and place, a time when parents would actually consider leaving a ten-year-old boy home alone.)

I Had to be Courageous

 Why did I need courage?  I knew deep down that even though I should not that I would most likely really, really, really enjoy wearing her clothes.  If I did that would make me the 'only boy in the whole world' who liked wearing girl's clothes  -- to my mind.  It would prove that I was in some way defective and would most certainly seal my fate and send me to hell.  My fears were not unfounded.  I did really enjoy wearing her clothes.  So much so that as I left her room, I promised myself I would never do it again.  I needed to make this promise as if I did not I would surely do it again.  The promise however did not protect me from a life of sin.  I broke the promise I made and return to her room, her closet, her clothes  -- her life.

I feel I have much more to say on this topic but I will leave it there for now as this is already considerably longer than I had wanted it to be.