Debbi Richards' Journey Into The World Of Crossdressing
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The Early Years
I was a child of no more than 10 years of age when I discovered something about myself. I absolutely adored women's clothing, especially high heel shoes and hose. Our family was of modest means and to help with household expenses, my parents decided to rent a spare bedroom to a young "career girl". I think she was just a secretary, but it sounded nice. After all, this was 1961! She was totally into clothes. I never knew that anyone could have so many clothes and the crown jewels of her wardrobe were several pairs of 3 inch spike heel pumps. I was always strangely fascinated at how she managed to walk in them without falling down and I also had this odd sensation that struck me whenever I saw her wear them. And the sensation, which I couldn't explain at the time, wasn't unpleasant, either.
Then
it happened. Everyone was away from home and I was left with the
objects of my fascination and oh so little time. So I headed for
"her" bedroom and the closet, prepared to search for the
shoes
I so desperately wanted to wear. Awaiting me were the shoes on the
floor beside the bed. With my heart pounding so loud I knew someone
would hear it, I picked up the shoes and smelled the fine leather and
felt the smoothness and softness of the light blue leather lining.
Then, I slipped one of the shoes on my foot and it fit almost
perfectly. The unexplainable sensation I felt when I saw her wear
them returned and flooded through my body. On went the other shoe and
then I found myself in total sensory overload. Later forays saw hose,
panties and slips added to the mix. I was in heaven!
Too soon after my discovery, our "career girl" decided to get married, so I was off to other diversions...or so I thought. Our neighbor's daughter was six years older than me and an only child just as I was. She was almost 16 and was learning about make-up and since there was no one else around to practice with it soon became my joy to be her "guinea pig". She decided to perfect her nail polishing techniques using my nails, which was just fine with me. I thought they looked wonderful! Then came the make-up and all the trappings. I found out at an early age that make-up can make a big difference in the way a girl looks. I always wanted to go home and show off my "new look" but she always insisted on removing the polish and make-up before I went home. Early in my young life, I had the opportunity to satisfy my feminine desires with willing accomplices. Little did they know.
The 1960's and 70's
Years passed and the desire to do femme things passed as well. Then came puberty and the hormone rush. At the same time I began to notice girls...bigtime! Not only was I interested in them, but I was also interested in what they were wearing. The cute sweaters, the pleated skirts, the suntan pantyhose and colorful Pappagallo flats made my heart race. And how I wished that I could wear what they were wearing! The urge was as strong as it had ever been, but I still didn't understand the meaning of it. And the idea of having anything feminine at home was out of the question.
As I got older, I had the "summer job" to earn money for school and "boy" clothes and consequently elected not to take vacations with my parents. During their absence, I would have the time of my young life. First, I'd head for the K-Mart and buy any size 10 shoe that looked like it would fit me. The reason I bought size 10 was that it was the largest size they had. Then I'd add a pair of panties and pantyhose. I would head home every night after work and enjoy my treasures until my parents returned. Then, it was off to the nearest dumpster to discard my prized possessions. My mother was the consummate snoop, so I never contemplated hiding my shoes, panties and hose. No matter where I would have hidden them, she would have found them and it just simply wasn't worth the risk. This scenario repeated itself many times over the next five years until after my college graduation and I moved into my own apartment.
The freedom to explore my proclivity for women's clothing was not wasted when I got my own place. I built my wardrobe from just shoes and hose to skirts, blouses and various articles of lingerie. Buying the stuff was the hardest thing to do, but I learned that having a wedding ring made it a lot easier...or at least I thought so. I had been given my grandfather's wedding ring following his death, and I decided to put it to use when I shopped. It was a virtual honeymoon for the next two years. Then suddenly, there came the overwhelming urge to purge. All of my clothes hit the dumpster and I was eaten up with self-imposed guilt and shame for having indulged myself. I felt that I must be some kind of pervert to have these urges and needs, but I was afraid to ask for any help because I felt the need for feminine expression was a part of me that would never go away. This guilt and anguish would last for the next 17 years.
In 1976, I met the girl of my dreams. Smart, kind and pretty. She had my heart (she still does) and I felt that just maybe my dressing was just really a manifestation of needing a woman in my life. But deep down I knew the feelings of a definite feminine personality lingered along with the questions and the guilt. In my childhood, the prevailing opinion was that any male who dressed in women's clothing had to be gay. My family even thought that Milton Berle and Flip Wilson had to be a "little off the mark" for dressing up on their television shows. But I knew better. I knew me. I knew my sexual orientation was definitely heterosexual, but for some reason I had the need to express my feminine feelings in some way. That way had been dressing. I was on an emotional roller coaster, but tried hard not to let it show to the outside...not even to my wife.
The Epiphany
Then a change in career direction occurred in 1993. The change allowed me the opportunity to do some research on the feelings I had suppressed for years. The real light was shed when I gained access to the Internet. Then, I found that I was truly not alone in the world. With the career change also came the opportunity to experiment with things feminine and broaden my knowledge on the subject of heterosexual male crossdressing.
Fast
forward to 1998. By now, I had acquired a new wardrobe, some make-up,
a wig and lingerie. My situation allowed me opportunities to dress
and experiment with make-up. But then, I got
careless.
Once after trying to perfect my eyeliner application techniques, I
failed to remove all of it. When my wife arrived at home, guess what
she saw first? I just passed it off as grease from the car, as I had
just checked the oil and had rubbed my eye. Then came the discovery
of some remaining nail polish on another occasion. I truly think I
was trying to find a way to come out to my wife, but certainly not in
the right way. Then I decided to arm myself with the facts about
crossdressing and deal with it head-on. After 37 years, I had finally
accepted myself and my need to dress. Now it was time to tell my
partner in life.
It took more courage to tell my wife about my dressing than it took for me to ask her to marry me. I was so nervous, I could hardly stand it. With full speed ahead, I plowed through the uncharted waters of a full confession of who I was and how an integral part of my personality had been cloaked in darkness for these many years. The full range of human emotions were experienced by both of us, from tears to laughter. When I was finished, her reaction completely amazed me. But then she has been amazing me now for over 30 years. She said she actually hurt for me, having to deal with the mental anguish of something so intensely personal. February 2, 1998, ended with the emotional release I had been seeking nearly all my life.
I moved my clothes from the "hiding place" to my closet. Got some wonderful make-up tips from my wife and immediately went shopping for those "little things" that make the look complete. Since that fateful day, we've regularly shopped for
clothes and accessories for both of us (and have more fun than ever before doing it). And while we are both still learning about my feminine attributes, we are having a good time in the learning process. But most importantly, in the spring of 1998, I reached the
springtime of my life...who I truly am. I was accepted at home by the person
that means more than anything in the world to me and I found the fun that comes from associating with other persons whose gender expressions mirror my own.
The Journey Continues
In 2000, I had to take a secondary role in my local Tri-Ess group because business demands swallowed up much of my free time. Dressing was more an occasional event rather that a regular one. September, 2000 saw another trip to Atlanta (documented elsewhere on this site) for SCC2000. Following SCC 2000, I decided to take an active role in the planning and development of the conference. I became a part of the programming staff and worked to develop programs for crossdressers, which was a most rewarding experience.
The years 2001 and 2002 saw some unexpected twists in my transgendered life. I continued my involvement with the Southern Comfort Conference in working on the programming side. In 2001, it became more apparent to me that the support group I had helped build over the last three years wanted to go into a direction that I fundamentally disagreed was in its best interest. However, being one vote and a single voice I continued my support for the group but being mindful of the direction at all times. At Christmas, 2001, the founding members of SRD were honored at the group's annual Christmas party...little did I know that it would be the last time I would attend a function with that particular group.
In January, 2002, I started an email list among several ladies who all enjoyed each other's company. What grew from that listserver was the Capitol Ladies Society! The CLS is purely an "invitation only" social group for friendship and good times. We met periodically in 2002 but now meet monthly and our membership has grown to 14 members. Again, it's now fun to go out with my friends and enjoy the special bond that all transgendered people have.
From spending the majority of my life supressing my transgendered nature to spending the last 12 years coming into an understanding of my feelings, I have found fulfillment beyond belief by being able to live life (even if just a little bit) as who I truly am. And the journey continues!
Questions?

© 2010 Debbi Richards