Most people who practice crossdressing discovered themselves in their teens.
Crossdressing is the practice of wearing clothes and accessories belonging to the opposite sex. In this article, we’ll be talking specifically about guys who like to dress like girls.
Although some are fascinated by women’s clothing already in childhood or only in adulthood, probably the stage where crossdressing emerges is in adolescence – or even in pre-adolescence. But why?
This is the phase where young people begin to develop and the differences between boys and girls become more evident, for example: Boys have a wider body, more body hair and a deeper voice as they grow older. Girls get slimmer waists, develop breasts, start wearing bras and learn to apply makeup.
When I was about 11 years old, I noticed that girls at school started wearing bras and I was curious. I decided to secretly try on a bra from my sister. I enjoyed the experience and did it other times. On cold days, I would go to school wearing a bra under various clothes.
As an adult, I started buying my own bras and decided to try new things, like panties, tights and dresses. But my entry point into crossdressing was when I was a teenager hiding in my sister’s bra.
Crossdressing in adolescence, like anything that is out of supposed standards, is still a challenge in families and society. Many parents do not understand how their child can like women’s clothing, and society does not accept this as something “normal”…
We are not talking here about transsexuality, when boys identify with the female gender, but about boys who like to wear feminine clothes and accessories. They may like to do it out of curiosity, because they find women’s clothing more beautiful, because they like the feeling of wearing it or because they feel some kind of attraction, for example. It is not a disorder, but a form of personal expression.
This is an issue that needs to be addressed because many young people do not know what to do when they discover that they like women’s clothing and many parents do not know how to deal with it.
Teenagers can come into conflict with themselves when they discover that they like women’s clothing and have emotions of shame and guilt, for example. They may also feel confused or repressed for not fitting into a supposed standard imposed by society, which could also hurt them through prejudice.
Parents can fight with their children if they discover or even catch them wearing women’s clothing. Many do not accept it and end up repressing it for believing that it goes against their beliefs and for fear of society’s reaction.
Probably many crossdressers who discovered themselves as teenagers would have been happier if they could have expressed themselves confidently at that time. But surely many would be confused if their children also expressed this desire.
It is necessary that people have access to information to better understand crossdressing and that it is not a disease or disorder. With more information, young people, their families and society will be able to understand each other better. In addition, therapy is also a good way for young people and their families to understand and get to know each other better.
* When did you discover you liked crossdressing?
* How did your family deal with your crossdressing?
* What would you do if your son was into crossdressing?
Sincerely,
Marie Claire
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I started wearing Women’s clothes when I was 12 years old, It started with my sisters slip and then moved to pantyhose and my Mothers panties and Bra’s, My Mother confronted me when I was 15 and I denied it but she knew I was wearing hers and my sisters clothes. If I had a Son who cross dressed I would tell him that is Ok and to do what he felt was right for him.
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Very good!
@Marie Claire I, too, was 11 or 12.  I was folding clothes and found myself folding my sister’s pink panties.  They were much softer and different than mine.  I took them and tried them later on in the barn.  I continued with the experience, bra, pantyhose, shoes, dresses, shorts, tops wigs, then makeup and jewelry.  By 15, I was skipping school to stay home and dress up! I believe my mom knew but never approached me with it.  No one else knew that I know.  My spouse knows today and disapproves so I do not do it in front of… Read more »
So interesting!
It occurs to me that the experience of being a “teenager" has changed enormously since I was at that stage back in the late 1950s. Women’s clothes have also changed, as have attitudes to gender diversity and accessibility of information – and so many other things. I’m not sure whether, in 2024, if I was a teenager, I would think much about cross-dressing because women now wear clothes that, to me, don’t have much appeal and are often almost identical to male clothes. It was very different when I was thirteen. I don’t think I ever wanted to become a… Read more »
Nice memories!
I started dressing very young, I know it was before I was 9, as we moved from one side of London to the other and I was at least trying on girls clothes then. It became much more prevalent in my teenage years, usually my sisters clothes when I was at home alone. Two things I really remember from then, it wan not something a young boy should do and as a result I had to keep it a secret. This was the 1960’s and there was no information available at all, there may have been support organisations but I… Read more »
The world still has a lot to evolve!
I was dressed as a girl for the first 3 years of my life as I had an older sister and money was tight. I was into lipstick as a toddler.
Bu age 10 I had my first bra and was dressing en femme by 14 when I could. I tried a few arrempts to stop but that did not last long. The older I became the stronger the desire to dress as a woman. I am now 75 and continue to dress.
Good!