Crossdressing — The Perfect Solution

crossdressing home

This was our home from midway through my third grade year until after the completin of my junior year of high school. It was in this house that I started crossdressing.

I was ten years old (give or take a year) when the idea of dressing up in Cheri’s clothes took form in my mind as a solution for my unhappiness.  The seed of the idea was originally planted by Bruce.  We were heading upstairs to our shared bedroom when he offered to share a secret with me.  He had overheard our older brother being scolded by our parents.  He had been caught wearing some of our sister’s clothes.

Crossdressing is not a term neither of us would have used to describe his behavior.  Nor was it a term I used once I started dressing up in her clothes.  It could also be suggested that I did not know at the time that I was unhappy.  However, as soon as I heard what Mike had done, I knew I wanted to do it to.

In all fairness to Mike, I have no way of knowing whether or not this story was true.  It is just as likely that Bruce had been caught and scolded and was trying to get ahead of any story about himself by changing the culprit in the story.  It may even had been a total fabrication to make Mike look bad.  The two of them often did not get along.  Whatever may be the truth about this shared secret that day it gave new meaning to my life.

Upon hearing of this scolding, I chuckled as was expected of me.   We may have even shared a couple of jokes about how funny that had to be.  However, to me, the seed of an idea that it planted in my head was like a gift from God.  It was an oblivious solution to feelings I had and yet had never been able to understand.  It was so oblivious I can recall asking of myself, ‘Why didn’t I think of that myself?”

It should be noted that I am not suggesting that my feelings had anything to do with being a girl.  And I am not real certain I would have described myself as an unhappy child.  However, the idea of dressing up in some of Cheri’s clothes gave me hope that somehow life would and could get better.

Making It Happen Not So Easy

At the time, we did not live in a big house.  There was a bedroom downstairs where my parents slept.  There were only three bedroom upstairs.  Cheri as the only daughter got one bedroom.  Mike as the oldest son normally had the second bedroom.  The third bedroom was left for the three remaining sons — myself and my two younger brothers.  The second floor window on the left in the image was one of two windows in that bedroom.  The room ran  the full depth of the house so it was quite large.  It was however still a shared bedroom.

I mentioned this because as a child of ten years old with brothers and a sister ranging in age from 6 to 11 there were not many opportunities for me to have time to myself.  Nor was it just a question of opportunity that kept me from going to Cheri’s room and trying on some of her dresses.  It was also a question of courage.  There are some boys — maybe Mike — who might visit their sister’s closet simply as an act off curiosity.  How would it feel to wear a dress?   For me there was never any doubt in my mind as to how it might feel.  I knew it would feel great.  I knew I would love the experience.  I suspect I also knew that if I gave into temptation even once, that it would be a temptation I would be unable to resist a second and third time.  I was certain that I had to be the only boy in the world who wanted to wear dresses — and be a girl.

When Did My Crossdressing Begin?

skipping school

After I returned home from the hospital there were several days when I would feign illness just so I could stay home and indulge my crossdressing desires after everyone was gone.

I was eight years old and in the third grade when we moved into the house pictured so I know I was older than eight.  In October of my sixth grade year, when I was eleven, I had appendicits and spent one month in a Spokane hospital.  As it had been a quite serious health crisis for me, my parents decided to keep me out of school until after the Christmas holiday.

While the first couple weeks of this recovery time had me too weak to get out of bed, I have memories of an eagerness to get well enough that I could use my ‘vacation’ time to once again get back to ‘dressing up.’  ‘Dressing up’ is the how I thought of my secret passion as I was not yet familiar with the term crossdressing.  As I wanted to get back to dressing up, it seems logical to conclude I was dressing up before the appendicitis.

When I was in the fifth grade, I often had to be excused from PE classes and recess activities because of my stomach pains.  I was often mocked by my classmates for these excused absences.  Sometimes the pain was so intense that I could not even go to school.   I am sure it was on one of these days when I stayed home from school that I first found the courage — and being home alone as both of my parents worked — the opportunity to visit Cheri’s room and try on some of her dresses.

It does not seem likely it would have happened during the summer months.  And while there was the month of September before I had the appendicitis in October, that does not feel right to me.  So as best as I can conclude it was in the spring of y fifth grade year, in the month immediately proceeding my eleventh birthday in June.


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