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?

 

Sincerely,

Marie Claire

EnFemme

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Katerina Witt
Lady
Member
7 months 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
Lady
Member
7 months 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 »

Ellie Williams
Lady
Member
28 days ago

The first time i ever dressed up i was around 9 yo, was always curious and kind of jealous of other girls in dresses and skirt before that (and after to be honest, i also wish i could’ve worn a skirt or leggings to school…) no one in my family knows about my girly side yet, if i ever have a son and he also likes crossdressing i would be as supportive as i hope my mom is when she inevitably finds out! i would even buy new outfits with him!

Veronica Vallys
Baroness
Member
28 days ago

I discovered crossdressing, like many others, around the age of 12. It started with my mom’s lingerie and then experimenting further with her work clothes. She wore a lot of skirts and satin blouses. The feeling of my legs encased in nylon pantyhose rubbing against the lining of a skirt was divine. To this day, I can’t have enough of it. Still it created quite a lot of confusion and shame. I was found wearing one of my mom’s bras by my dad once as he unexpectedly arrived home early one day. I explained sobbing that it was the first… Read more »

Samantha Marie
Member
Active Member
25 days ago

I wished I had seen this topic when I first joined , so much to read and reply to xx

Samantha Marie
Member
Active Member
25 days ago
Reply to  Marie Claire

Yes , will catch up on the comments later and certainly will post my thoughts .Thank you Marie Claire

Steffi Randolph
Lady
25 days ago

@marieclaire2  I guess I was probably about 12 yo, but I can’t verify that.  All I do know is that I was old enough to be left at home alone in the evenings.  I had had fantasies when I was younger, but being home alone allowed me to try on panties, girdles and bras.  I was never “caught", but that isn’t to say that mom didn’t know.  She may have been unwilling or unable to confront me. I got married without telling my wife.  I thought that is would go away once I got married and had as much sex… Read more »

Natalie Jones
Lady
Member
24 days ago

I’m 66 and began crossdressing in the late 1960’s. I had zero I idea what and why I was doing it. I just know I enjoyed how I felt when I put on something feminine. It was a complete contradiction of everything else I felt. Other than this I was a typical boy doing all the things boys do. I didn’t even know what to call this secret thing I did and wanted to do. Unlike today there was no information out there. At Least not where I could find it. Occasionally I would read something in the newspaper about… Read more »

Stephanie York
Lady
Member
23 days ago

@Marie Claire I was 14 when I started. It was the early 1970’s. I had long hair and was often mistaken for a girl. One day I was curious how I would look fully dressed I was going to be home alone. I tried on my sisters and Mom’s clothes and dressed frequently. Loved the experience.
Never was caught.
Probably would be understanding if my son crossdressed
 

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