Crossdressing in teenage: discoveries, doubts and insecurities

[marieclaire]

Crossdressing in teenage: discoveries, doubts and insecurities


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?

[Karren H]

I started when I was 7 and my parents never found out. Our son is gay and we handled that just fine. His partner just came out trans. Just another twist and turn in modern life.

[Saralee]

I can't say how old I was for sure but definitely grade school age maybe 7 or 8. My mom had these navy blue leather slip on sandals with heels in the back. They just looked neat and so I just tried them on. They were easy to slip on and so I just practiced walking around the living room in them. I remember I heard my older sister coming so I had to hide the shoes under a chair really fast. My sister used to tease me relentlessly about girls and if she would have seen that it would have been the end. My family never knew as far as I know. I never would have wanted them to know.

[bridget thronton]

About age 13 (mother's clothes). Never caught by parents. If my kids cross dressed I would have supported them.

[alwayshave]

I started dressing when I was 4 or 5 years old.

[Jillcder]

With my mothers help i wore a dress at one of my elementary schools Halloween party after that I remember my early teens really kicking in strong I dressed in my sisters clothes when everyone was out of the house. To the best of my knowledge they did not know I dressed.
I do not have any sons but I firmly believe I would be accepting.

[Bea_]

* When did you discover you liked crossdressing?
I didn't officially crossdress until my mid-fifties. In my early teens, I'd put on my mom's or my sister's bras that were left to dry in the bathroom to have something feminine to aim my testosterone at. There was no sense of wanting to wear a bra other than that. My mom nor my sister had any style that I'd want to emulate.

My wife was beautiful when I met her (and still is) and her style was as mesmerizing as her smile. I never really considered wearing her clothes for the first few decades. A couple of times in my thirties, I tried on various items, but it was just curiosity that was satisfied and forgotten. (I really wish I still had my fifty pound lighter physique from my thirties. Feminine options would be MUCH greater now)

In my fifties, after some extensive, drawn out trauma, I developed an interest in wearing panties and discussed it with my wife. She bought me my first nice panties and things have developed from there.

* How did your family deal with your crossdressing?
N/A

* What would you do if your son was into crossdressing?
My son was grown and married by the time I first started dressing so it would have been unfamiliar territory for me.

I think I'd have tried to make as much of a non-issue as possible. I'm afraid his mother would have shamed him badly if that had ever come to light. I think I'd have run interference in that respect, even if I didn't understand it. I'd also warn him that that path would not be an easy one.

[Michaela Jane]

I didn't begin crossdressing until I was in my early 50s. It's strange how I started because I was looking for a particular underwear item & couldn't find anything I liked. Out of the blue, I asked my wife if she minded me looking at the womens dept to see if they had any that appealed to me. She said that was OK & I found exactly what I wanted. That was the start of my slippery slope.

[Celee]

I was 9 or 10 when I started. I found a pair of my mom?s panties in the laundry hamper and curiosity got the best of me. I would sneak them into my room in the middle of the night. When I was a couple of years older I would stay home by myself and thats when it really started.

[tifftg]

I was 12 or 13 when I started experimenting first with my mother's and then my sister's clothes. My mother caught me once when I was 15 they came home early from a trip. I told her it was the first time and she never discussed it again and they never caught me again.

My son is gay and we supported him.

[JesseVF]

So early I don?t know for sure - around 5 give or take. With three older sisters and mom there was ample opportunity to play and things just felt good/right. Always felt I should have boobs.
I think my sisters may have noticed things - one time for sure when she found one of their lingerie items under my bed where I had forgotten about it. However nothing ever said to me. Also my mom found me playing around with sisters bathing suits once but a stern ?stay away from those? was it.
Hard to say exactly how to handle the hypothetical if my son was taking part - depends on the specifics - but would certainly support him in a positive way as much as possible- at least it?s better now than the 60?s world.

[MarinaTwelve200]

One bad thing, especially in past decades, (and often still floating around in adolescent circles) is that "Cross dressing means you are gay" . Many "uneducated" adults still believe that., combined with Categorizing Gay, Transgenderisim and Cross dressing in the SAME "basket". Can make for a difficult time for those who discover they like cross-dressing. Kids (and often their parents) should KNOW the definitions of each of those terms, and not get freaked out over it. Well, of course all three groups cross-dress (the verb) but for drastically different psychological reasons. Even if one is not entirely "woke" and is prejudiced against "gays" for example, there is an "out" if they decide they are only a "crossdresser". I think you get the idea. It is the Myths and uncertainties that vex beginning crossdressers and how much they (or their parents) subscribe to them. Fortunately, at age 13, I was a "bookish " kid, so I hit the psychology books and found out WHAT I was, and learned the correct definitions before I got too upset and began to "suffer" out of ignorance as to my proclivities. I stayed in the closet and kept things secret, though because I KNEW my parents, schoolmates, and the public in general, were generally ignorant, and highly intolerant. I didn't wanna be persecuted, abused and called something I was not, because others were too lazy to learn the proper definitions. At least I was comfortable with myself.

In the mid 1960s, Most people I knew and my parents were highly hostile to "Queers" the catch-all term for Gays, Transsexuals, cross-dressers, etc. And were all defined the same, "A man who thinks he is a woman" characterized by acting effeminate, dressing like a female and prone to abuse kids. Having to deal with such a definition One can easily see why a young cross-dresser can be concerned, and in my opinion, HAD to be insane to actually go "public" with it.

I Still am in the closet, although I have gone out on Halloween and for a "Womanless beauty contest at church.

If my son got into Cross-dressing, I would not freak out. I would first ask him questions to determine if he is only a crossdresser, or something MORE "complex" like Gay or TS. I would make sure he had his definitions straight to avoid personal (and needless) "conflicts" within himself, warn him of the RISKS he would be taking if others found out about his "hobby" and let him take his own chances if he wanted to go out. If he gets into "difficulty", he wouldn't say I didn't warn him.

If he actually was to be Gay or TS, then he could get proper "counseling" to deal with his situation. I could live with that. What I would NOT want is for him to think he WAS Gay or TS and not really be. It could lead to a hard life of abuse, terrible mistakes, all for nothing.

[NancySue]

I was 6, when our next door sisters, who enjoyed playing ?dress up?. One rainy day, they invited me to join them. At first, I had no interest. That is until I found nylon stockings. They helped me slip them on. I?ll never forget the electricity. I acted like it was no big deal, but obviously it was. I wore them as often as possible. As we know, CDing is progressive. Over the years my dressing included more and more. Now retired, I dress daily, panties, bra and hose.
My parents never knew. I told my wife before we wed. She?s totally supportive.
I have two daughters, neither know.

[Amanda77]

As i have said before, i started around 12. Was looking for something in the closet across the hall from my room and found a box of my older sisters (i have 3 older sisters) outgrown clothes including undergarments. Curiosity got the better of me and took a training bra and panties to my room and tried them on and loved them.
And it snowballed from there.
Did i get caught, well mom found them in my room and put them back several times but didn't say anything.
If i had a son that crossdressed i would support him totally.

[sara66]

I started with a bra when I was 4 or 5.

I was only caught in the act once when I was about 8 or 9. Mom just said those are not yours, and left it at that. I am nearly 100% sure mom knew. She kind of hinted at it a few times. I am sure mom would have been fine with it as long I stopped "borrowing" her and my sister's things. I wish my mom was still around, I would have really like to talk with her about this. I also believe she might have thought I might be gay. I was a late bloomer and did have my first real date until I was 28 and didn't get married until I was 39. My dad would have freaked out a little. I have found out my dad was probably bi-sexual and had some mental heath issues. I have never been sure if they were related or wholly unrelated.

If I had a son that we caught dressing I would have my wife speak with him. I would have her let him know he is not alone and we still love him. I think having dad or any older male speak with him would shut him down. I know I would have related better to my mother.
I would not let him know I was was also a crossdressers. That would be weird for everyone. Your kids don't need to know your business.

We are lucky we have the internet today. I remember feeling I was alone in wanting to wear women's. We still don't know why but everyone's journey is a little deferent.
Sara

[Becky Bloodstone]

I was fascinated by crossdressing very young. I always loved seeing RuPaul on TV. I never did anything much when I was younger. I don't have a sister and my mom's stuff was way to big of course. My dad wasn't a very nice person and would definitely not have been understanding with something like that so I could only imagine would would have happened if I did make an attempt and got caught. I mostly stayed with small things like a bracelet or a cheap ring a girl would wear, i had a ankle bracelet that i loved and wore throughout my teenage years. I didn't start fully dressing until I was 29. My family doesn't know and if I found out my son was crossdressing I would be supportive.

[Stephanie47]

"When did you discover you liked crossdressing?

When I first dabbled in my mother's lingerie draw I hated it! I felt disgusted. I was filled with self loathing. Why was I doing it? Yes, there was an unknown attraction. It did not make sense that a teenage boy who lusted after unobtainable starlets of the movies or neighborhood young women would feel the need to wear his mother's clothing (I had no sisters or female cousins)?

"How did your family deal with your crossdressing?

My family, mother and father, suspected and tried to catch me in the act. They never confronted me with their suspicions; Why was the strap on my mother's sole black bra broken?" I am sure, if I had been caught, I would have been tossed out of the home when I turned eighteen. There attempts to catch me was just before my eighteenth birthday.

[Lorna]

I have, I think, reached the end of my cross-dressing life (but not, I hope, life itself!) and can look back over many years to when, as MarieClaire wrote, I "discovered cross-dressing in my teens". We all have different approaches nd experiences and things have changed so much in those intervening years. I have started writing what is supposed to be a summary of my 65+ years of dressing and wonder whether I should post it on this forum. Inevitably it will be a long post - but probably my last one as an active contributor, though I would like to go on enjoying reading, and occasionally commenting on others' posts.
Would such a "biographical" summary - even a long one - be acceptable? I wouldn't want to offend anyone.

[Sometimes Steffi]

Why don't you post in in shorter chapters? Like some of the others under "Writers Society" sub-forum?

[Lorna]

Thanks Sometimes Steffi. I would be quite happy to do that.

[Gillian Gigs]

When did you discover you liked crossdressing?
I started off in little differently than most of us. Initially girls clothes were used as a punishment when I was bad, always with nylon panties. As my much older sisters married, I moved into the basement bedroom across from the laundry room. I was around 12, seeing all those items that were once a punishment hanging to dry after laundry day. Growing up, I had continual thoughts and fantasies about girls clothing, especially dreams. I felt drawn to once again wear what had been instruments of punishment. I eventually moved on to my mothers dresser drawers, and all of her clothing.

How did your family deal with your crossdressing?
I thought that no one could know about my activities, but now I realize that my mum must have known about it. As I would regularly raid her dresser, I must not have returned, or possibly soiled some of her items. One day I found that my favourite items had been removed from their regular place. I found them in another drawer. They would be washed regularly and returned to this new place. Not a single word was ever mentioned to me. It never occurred to me what was happening until many years later. She would occasionally discard some of her old clothes into a closet in the basement also. I always thought that if anyone knew, I would be getting punished and grounded for 'life' by my dad.

What would you do if your son was into crossdressing?
I would talk about the mess that comes with this habit/life style. I would talk about the guilt, shame and social issues that surround crossdressing. I have often wondered how things could possibly have been different if I had known what I was getting myself into. I would let him know how important, as well as how difficult it might be to find an understanding, and accepting spouse. I would impress how important it is to be honest and open with a potential spouse before marriage. Teach him that compromise is an important part of a marriage and that he can't always get what he wants.

[Jessica Secret]

When did you discover you liked crossdressing?

I was probably 11 or 12 when I discovered my mom's romantic nighties & lingerie, and I was immediately hooked. I'll never forget trying it on and being in a state of ecstasy, it was incredible. I started wearing romantic lingerie or satin pjs to bed every night at 16 and I've never looked back.


How did your family deal with your crossdressing?

Didn't know until I was 18, my mother supported me and even bought me some lingerie for my 18th birthday. Rest of my family never knew.


What would you do if your son was into crossdressing?

I would fully support him in any way I could.

[Heather76]

* When did you discover you liked crossdressing?

I guess the correct answer is around age 12 or 13. When home alone, (rare with 2 brothers in the home) I would put on a bra of my mom's. I would also put on her girdles. This was in the late 50s when girdles were quite common. I stopped this when I was 16 and started dating. I was then married at age 20, joined the Navy, and was discharged when I was 24. Sometimes between ages 24 and 35 I would on rare occasions put on my wife's pantyhose. I was always aroused when doing this. However, I really didn't realize this constituted cross dressing. I always thought of cross dressing as doing the whole "en femme" thing.

* How did your family deal with your crossdressing?

Nobody ever knew of these activities. I would guess during my youth I likely put on my mom's things 10 times in 3 or 4 years. I probably put on my 1st wife's pantyhose 5 to 10 times in 17 years. I didn't start truly cross dressing until my 2nd wife and I were married 36 + years and I was 74. She's not a fan but accepts that I CD.

* What would you do if your son was into crossdressing?

My son is now 50 years old. If he told me he enjoyed cross dressing, I'd throw my closet door open and suggest we have a girls' day out together. While we never know 100% what our children do, I'd be about 99% certain he's not into CDing.

In retrospect, I wish CDing was socially acceptable with no stigma attached to it for the past 70 years. I believe I may have started CDing regularly in my teen years and lived as a MIAD the past 60 years.

[Bobbysue]

Not sure how old I was. I'd wear my moms full slip it fit like a maxi dress and her heels. The I found how panties fellt.They never said anything but mom had to know. I probably didn't get everything back in place.

[Claire M]

*When did you discover you liked crossdressing? When I was 13, I saw a pair of my sister's panties on the bathroom floor. At first I was just curious but as soon as i picked them up, I HAD to know how wearing them felt. A couple weeks later it was the same with her bra. And so it went with pantyhose, dresses, makeup,....

* How did your family deal with your crossdressing? My parents and siblings never knew. My children also don't know ... only my wife and we don't talk about it much.

* What would you do if your son was into crossdressing? My son is now in his 30s. If he's dressing, it's his deal but I would support him. My only advice would be to not hide it in his relationships. If I had found out when he was a kid I would still support him and tell him he wasn't doing anything wrong. But I would also educate him on the hard realities of our society. It's just clothes but a lot of people see it as something dirty and perverse. If you put this out there, be ready for the consequences.