Why I Crossdress

[Larissa Cassandra]

After many years of wondering why I'm so different from most other men, I think I've finally figured out why I've been drawn to crossdressing and why I enjoy it so much. It's actually fairly simple, and there are only two parts to it.

1. As I've mentioned in other posts, I'm almost certain my mother would have preferred to have a girl as her second child (though she never told me that). She'd had a miscarriage and my older brother before me. She always talked "baby talk" to me, even just "kidding around" after I'd grown up. She was quite the girly girl herself, always in dresses and heels, with full makeup and always perfume (I remember Heaven Sent and Wind Song). I suspect she might have dressed me up in girls' clothes when I was a baby or toddler, but I don't have any specific memories. If she were still alive, I would ask her, but I missed that opportunity.

My mother left my father, brother and me for another man when I was only 11 years old, so I lost her feminine presence in our household. Everything was manly and macho all the time. My father was great in taking care of us, but he was the old-school John Wayne-type man's man. So missing exposure to anything feminine has made me quite curious about girls and women, and later when I could try clothes and makeup, it was a lot of fun and opened a whole new world to me.

2. About a year or so after my mother left, I started going through puberty and paying a LOT of attention to girls. I had several girlfriends throughout high school, but never any of the "high maintenance" girls, like the ones in all the slick magazine ads and TV commercials. Those were the ones who were the sexiest, according to the advertising industry, so of course I found them very alluring. So when I was able to wear the few female things I'd obtained (that could be another thread!) and put on makeup, it was a substitute for the sexy young women in the ads, and the "hottest" girls in school. I was very shy as a teenager, and those "hot" girls just weren't my type anyway, personality-wise. BUT, the image of the ultra-feminine woman dressed in a beautiful dress with jewelry, makeup, long flowing hair, heels, and (I imagined) sweet-smelling perfume was very attractive to me. So when I was able to imitate some of that look on myself, it was a big turn on.

So, to summarize, missing out on a feminine presence in my home, and then going through puberty with my increased curiosity and the erotic images in my mind, seem to have cemented in my mind a love of everything feminine and a desire to emulate a feminine persona. But the strong male influences from those years living with my father and brother, then 4 years in the military, make it difficult to enjoy my feminine side without feeling some shame and embarrassment. This is why I don't dress as often as I would like to, even though I have a very accepting and supporting wife.

Anyone have similar experiences or think there might have been other influences in my life that you had, which may have contributed to my crossdressing desires?

Hugs,
Larissa