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.

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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?



Marie Claire

En Femme Style

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Katerina Witt
1 month ago

 When did you discover you liked crossdressing? Like many, I discovered I liked crossdressing in my early teens – probably around 12 or 13. How did your family deal with your crossdressing? My family did not and does not know about my crossdressing. If they found out – some would be okay with it. Others…not! What would you do if your son was into crossdressing? I would tell him that I crossdressed as boy, and it is totally okay. I would try to alleviate any shame or embarrassment, which I felt a huge amount of when I crossdressed as a… Read more »

Natasha Krober
1 month ago

I was 8 years old. Stayed with my grandmother for a bit during school break. I wasn’t packed any pjs. My aunt lived with her mother. She phoned my mother on what to do. So. My aunt put me to bed with pantyhose and one of her teddy nightie. I was in heaven. I still remember that first night. From then onward. I would go to my parents bedroom and find my mother’s pantyhose. Wearing them around the house. Of course. Mom saying boys don’t wear them. But I sure did and I loved it. Later I wore moms pantyhose… Read more »

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