Well, I am not so “new here” myself, since I been a member of this forum, since 2005 and I have recently been enjoying, reading about your experiences and feelings of how others got started with Cross Dressing. The knowledge that we are not alone is very powerful and very comforting feeling and I thought that I might also share how I got started Cross Dressing. I do apologize for if being to long!
It was the early 1950's, growing up in Midwest, USA area. I had the father that worked hard all week and a mother that never learn to drive and stayed home most of the time, and she worked, as a babysitter, for other people’s children. I was the second oldest of five boys in our family. I was the typical kid who played football, baseball, and soccer and most other sports. My brothers and our neighbor friends would play “War” or “Cowboy and Indians”; and we would build “play forts” in the woods and generally lived the typical American life in the Midwest USA.
As I grew older I soon started to realize that I was not the normal or typical straight heterosexual male, as I was lead to believed most of my early years. As a young male child growing up, I was for some reason, more attracted female things like, their colorful clothing and the very different fabrics choices, and so this may have started my journey into Cross Dressing world, (I truly do not know how or when it first happened for sure) but I found myself wanting know how it felt to dress or try on various articles of feminine clothing. I do remember at that time most all women from always dressed very nicely when they went out and that often many had wore garter belts and girdles, stockings, silky nylon slips or petticoats, and high heels and maybe a strand of pearls when they went go out. Most all of the females were always in dresses and skirts for anything other than “sporty activity” clothing that many women dress in today’s world. That time was very different from now, there was no unisex clothing, and females always dressed like females, even their jeans were very different from the males.
I had no desire to try on my mothers and I had no sisters, but what I did have, was several single aunts and one aunt had stored a trunk, in our attic and upon discovering it, I had found that it was full of various articles of feminine clothing. Some of the clothing was made from silk and other included some very nice lace trim, including some erotic lingerie. Now with finding this trunk in our attic it made it very convent for me to now fulfill my desire and learn how it felt to dress feminine. Soon I found myself trying on the various different pieces of feminine apparel. I started with panties girdles and stockings, then bras, heels, slips, dresses, pearls, necklaces, etc. I always found myself dressing up feminine whenever I was left alone in the house, which probably began when I was around 8 or 9 years old. I was able to spend endless hours enjoying myself as I tried on various feminine treasures. I would often look at my young hairless body as I dressed feminine and I would have to admit that I did admire how I looked and how I felt when I dressed feminine. Seeing myself dressed feminine in the full length mirror stirred some strange excitement but very good feeling in my young body. These experiences, I am sure that they had created my interested cross dressing, at that time of my life but I some how the feeling had somehow faded as I started my early teen years and my desire to learn about the female body and about the pleasures that a young male could enjoy together with a young female.
Like many here, I had married my first wife in my early twenties, just because it was expected of me, at that time. I was still able to suppress most of my desire to dress feminine for many of those years, which followed. My first marriage ended and I was alone once again and I reflected back to my younger years and my experimenting with Cross Dressing but since this was after the seventies, there was more unisex clothing for males to choose from. No more need to have to just wear boring tightie whites we had a few more choices of color, fabric and cut of material, so I soon loaded up on my new found treasures.
After awhile, I met a truly wonderful and remarkable woman, the true love of my life. She was also divorced, and she also had some young daughters and we had married and life was great together, for almost 30 years. I was never able to tell my new wife about my missed opportunity in my life as to try to find myself and understand my desire as to Cross Dressing, for all the usual reasons. I did experiment from time to time with the occasional panties and sometimes, maybe a bra, but I always resisted as much as I could but I did feel some shame and guilt, but why, after all it was just clothing, maybe it was the reference about other Cross Dressers. I did know that somehow deep inside, she would understand and support my desires and all I had to do is just share my thoughts and desires with my wife but the opportunity never came up since she had become a victim of that dreaded disease, Cancer! I had come close to telling her about my desires once, when as she smiled as we gave each other a pedicure, including painting each others nails as we both tried to fight her Cancer together. I soon realize that it would only make our life considerably more difficult until she could beat the Cancer.
Now with her passing and all the girls have grown and all are living their own life’s, I have found that I truly missed being around all that estrogen and I found myself turning to dressing feminine to help replace some of those feelings and to help me get pass her death and it all has seemed to help, for myself I have fulfilled my life long desire to become a Cross Dresser.
As with many of you, the desire, ability, and willingness to Cross Dress has gotten stronger with age and in recent years I have pushed the envelope as much as possible while I am still being somewhat secretive to most people about it. I would have dearly loved to have shared my Cross Dressing desires and interests with my now, decease wife, but I somehow feel that she did know and she did understand. I now have a lot of time to pursue my own feminine desires as I choose. I have no illusions of passing publicly but I do try to look nice and I feel nice. I do enjoy my “feminine side.” Thanks for this great forum!