As a kid I was shy. I didn’t want to be, but I was. One day, I remember going to 1st grade wearing my mom’s stockings, holding them up with rubber bands—no pantyhose back then. In retrospect, it had been the wrong thing to do. My self-confidence was low. I blame it on my awkwardness, as my eyesight was very poor and I couldn’t see without my glasses.

As a teenager, I couldn’t get a girlfriend, not for my lack of trying. I figured somehow, everything would eventually work out; it didn’t. I told myself that girls could get anyone they wanted. They went for the jocks or the bad boys; I believed that’s what they desired. I was none of those, so to dull my pain, I turned to cigarettes and pot. Those were the times I would dress up. One day, when I was 17, I actually kissed a girl. The kiss lasted at least two minutes; I didn’t want to stop. She wrote me a love note, and I cherished it for a long time. I never saw her again.

Fast forward to age 26. I’d added drinking to my bad habits. I was hanging around all my high school friends, doing the same things they were. After work, we’d all go to a favorite bar, where I met a girl who worked there. She was interested in me, and we went out. We went to her house, and she coaxed me into her bed. I finally had sex with a woman at age 26. It kind of scared me, having never had a girlfriend before. I think she would have married me, but in the back of my head I heard Smoky Robinson singing, “You got to shop around. Don’t let the first one get you.” After nearly two months of going out, I just stopped calling her. I preferred hanging out with my friends.

I went on a few more dates with woman from an introduction service. Not much happened, all because I lacked experience. There was one girl I went out with though, who was really nice. We went to a baseball game, the beach, out to dinner, and I even met her parents. I screwed it up by hanging out with my friends instead of her. Like before, I stopped calling her. She was probably a keeper; I wasn’t smart enough to see it.

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When I reached 30, my friend and I went to the local bar. I met an older woman who was 53. We went out a few times; I really enjoyed myself. She had me call her each day before work. It tightened our relationship and I began to see her every day. This bar was the same bar that my dad went to. He knew who I was going out with and tried to warn me that this wasn’t a good decision. I didn’t care. I had a woman who wanted me. I couldn’t stay away. We met in June of 1988 and we’re still together today. I’m 60 and she’s 83. We no longer have sex, but I see her every day. It is more about the companionship than anything else. My wife has no idea I like to wear women clothes. She doesn’t like the idea of it either, having made comments over the years which kept me in the closet, so to speak.

Thirty years is a long time to be with someone. A lot of marriages don’t last that long. In December 2015, I decided to look for other crossdressers like me. That’s when I found CDH. It has become my way to talk about my own crossdressing issues. Prior to CDH, I had no one to talk to about what was on my mind, which brings me to today. My wife and I now have our own houses, so I CD at home. I have a lot of pent up feelings, and this site has been good for me.

As a teenager, I wanted a girlfriend. When other people talk about how they met their significant others, it’s mostly, “We met in high school or college.” That train sped right past me into my thirties. In hindsight, I suppose my wife has given me more than I ever thought I’d get out of a relationship. There has always been this other side of me that I had to suppress. There’s more to my story, the same as it is for everyone else who is a crossdresser. Thanks for letting me share a part of my life; I have to go call my wife before she calls me.


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    Rozalyne Richards
    Rozalyne Richards
    4 years ago

    Hi Misse thanks for sharing your story with us, i can relate to your story as mine is a little more or less the same, i started c/dressing at an early age then gave it up when i met my wife, it’s only in the last 10 or so years that the old feeling of dressing up have come back and the urges get stronger all the time, well i would love to hear more of your stories hun x hugs Rozalyne x

    skippy1965 Cynthia
    Trusted Member
    4 years ago

    Misse’, Your story is familiar. While not following the identical path you traveled, I too missed the dating experience in adolescence and early adulthood due partly to my paralyzing shyness and partly due to figuring no woman would want to date or marry a CD/TG person. I met and married my ex when I was 26 and thought the need to dress would go away ((yeah I know-stop laughing LOL). Obvious;y it didn’t-she found out a year in and almost left but stayed another 13 years while I tried but failed to give up this part of me. After the… Read more »

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