My first connection with female clothing was when I was about 8 years old with family & relatives at a lake resort north of my birth city of Toronto, Canada. I was born in 1941.
One day everyone had to be in a dress up contest & a male cousin & I were forced by our parents into wearing girls dresses. My cousin & I hated wearing a borrowed girls dress. Two years later the same relatives were visiting our home, cousin & I found our mothers talking in a bedroom & we noticed some lingerie around & we both picked an item and put it on. I never forgot my aunts silky satiny bra & the feel, it was so cool when I put it on, the mothers thought it was cute. I had a younger sister, so through my teen years when the family was out I could borrow some of her clothing and crossdress.
Having found opportunities to crossdress from male me to female, your mind becomes haunted with questions & anxiety...I shouldn't be doing this. I must have sinned so God won't like me. Guilt. But then again, my Protestant religion upbringing says God loves his children & is forgiving. Then I don't feel so bad. As a cd friend of mine says, this was the 50's, no support groups and afraid to tell anyone & fear of being caught.
Once I started working the want to dress girly vanished like it never was & stayed away for almost 25 years. In the mid 80's I had to buy a lingerie item for my Mom on her Christmas wish list. That put me in a reconnect by being in the lingerie dept., so I bought a couple of things for myself. After that occasionally over the years going to various dept. stores & fashion shops I slowly built up lingerie & a few dresses, tops, skirts & wowie pantyhose.
While dating & shortly after marrying Carolyn, having met in a Ski Club, we went to Halloween dances & twice I dressed up as a girl. For me to cross dress had been put so far back in the recess of my mind that I had forgotten that part of my life even existed and as some of the recent happenings triggered the past into the foreground I was remiss in not telling Carolyn this part of me existed at one time. That is the why I didn't tell Carolyn and for that I am sorry I didn't apprise her as it wasn't fair.
After internet searches in 2001 I discovered breast forms & a club in the GLBTQI village on Church St. in Toronto that was set up for cd, trans & so's, called Wild Side. I purchased my first set of breast forms, got a book on how to do make & cosmetics. I had my first makeover at WS & couldn't believe the face looking back in the mirror, I said, "Wow!" Jamie was born! WS has introduce me to many friends of all colors of the Pride stripe, the support has helped in my understand, education and growth as well as bringing my wife along into acceptance of Jamie, although it wasn't easy and I am blessed to have the amazing Carolyn as my wife. The internet has been huge in my further development. I am excited and love my life at 70 years of age & still have my slim teen figure.
If I can be of assistance to anyone coming through gender identity, I look forward sharing our slice of life here.