A Teenage Crossdresser

Every few weeks I get an email from a teenager who is struggling with crossdressing. They're looking for advice, sometimes sure of their transgender identity, other times coming to terms with the alien desire to wear clothes of the opposite sex. I think it's wonderful that the Internet allows us to explore the transgender demons inside us without letting on that we're anything but normal. Yet in many ways I'm conflicted about replying, because being a teenager and knowing about crossdressing is not something I can relate to.

Even though I've had the strange desire to wear woman's clothes since I was four years old, I didn't have a name or anyone to reach out to when I was a teenager. So I have limited experience in receiving advice early on in life, and then looking retrospectively to see how helpful that advice was.

I'll share some of my thoughts on the most common questions I've received from teenage crossdressers, and I encourage you to review the excellent resources provided for transgender youth by tsroadmap.com

I like to wear woman's clothes, am I a crossdresser? Maybe, maybe not. During the teenage years there is a lot going on as our bodies change and mature. Hormones are raging, as we begin to fully form our identity separate from our parents and family. During this stage of life things which seem vitally important today may not seem so important three years from now. We go through phases that seem to leave as quickly as they came.

By no means am I saying that your desire to wear woman's clothing, or your perceived identity as a member of the fairer sex is just a phase. Rather, you need to carefully examine your own feelings in light of the dramatic changes happening in your life. It may very well be that you are a crossdresser, and have been blessed to realize this so early in life. Only you know for certain whether you're a crossdresser, and it's okay to take a few months to figure it out.

Should I tell me parents? That's a tricky one. I haven't told my parents yet, even though I suspect my mom knew all along. There are few people in the world who care more about you than your parents. They want what is best for you, and can be your greatest allies as you explore your feminine side. Your parents could also end up harming your path to self discovery - a well intentioned parent may seek to cure you for fear of your future, or may have religious or moral objections to who you are that lends itself to destructive behavior. My advice would be to find another adult you feel safe confiding in. Perhaps it's an aunt you have a good relationship with, or a school counselor - someone who is able to place your needs ahead of the need to tell your parents without your consent. There is no guarantee that this person will have all the answers, or even any good answers, but talking with someone will help you figure out things for yourself as well.

Am I gay? Maybe, maybe not. Just because you enjoy wearing woman's clothes does not mean you're gay. Sexual preference (do you like boys or girls) and gender identity (do I identify as a boy or girl) are separate. In fact many crossdressers are heterosexual men who identify as male, but enjoy wearing woman's clothes on occasion.

How can I look better as a woman? If you're friends with a girl you trust, a great way to perfect your look is to practice and get her feedback. She's learning just like you are, and it can be a fun way to bond with someone. You'll also find many crossdressing tips right here on Crossdresser Heaven.

Where do you hide your feminine things? It's hard to find a place at home that is truly private. Even seemingly safe hiding places such as under your bed, in a suitcase full of regular clothes at the bottom of your closet are susceptible to accidental discovery (the day your mom decides to do laundry and turn over your bed, or go through old clothes looking for something to give to goodwill). The best hiding place is out in the open after your parents know, but this isn't always an option. A pile of 'your stuff' is usually a great hiding place - the box that holds your CD collection, or in a cupboard behind school text books. Look for a place that someone else is unlikely to have reason to go.

How can I remove makeup before my parents get home? I remember the first time I tried on my mother's lipstick I spent 30 minutes furiously scrubbing to try and get it off before she got back home. All the furious scrubbing made blood rush to my lips, so they looked red even though the lipstick was long gone. The best way to remove makeup is with makeup remover. Your mom probably has some, but if you're unsure you can buy eye makeup remover at any drug store. This will remove eye shadow, mascara, and can even be used to take off lipstick. Most blush and foundation should come off with a good face wash.

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26 comments

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  2. Jesse 17 April, 2013 at 18:48 Reply

    I am 14 years old and I have had this desire to crossdress for 2 years. The only reason I haven’t is because I don’t have any women’s clothing, my moms clothes don’t fit me and she doesn’t wear make up (plus I think it would violate her in a way) and I am to scared to tell anyone, but I want to know what it’s like to crossdress. I don’t know where to start so any help is appreciated

  3. unkown 30 December, 2011 at 01:39 Reply

    I have been crossdressing when sense I was 15, I first started by trying on mom’s bra’s & panties and later developed growing my experience. I tried everything I could get my hands on. Nobody knows my secret life but me. In private i fully dress up, but i wear my normal clothes & just wear panties underneath when i leave the house on my own. I still wear panties till this day. Thanks for reading.

  4. rya 16 November, 2010 at 12:50 Reply

    im 189 and have been doing it off and on for about 3 years and im just getting big into it and i want help with it :( like person to person nut i cant tell anit one that knows me

    • Alexis 19 November, 2010 at 07:19 Reply

      It's pretty hard to go through life knowing if someone will judge you. I lived for nearly 16 years in fear because my mother said they kill people like me off. I have a wife who knows my situation and I must say she thinks I look better as a woman, (I am 26 now), than a man. I even look good in skinny jeans and a nice blouse top. I wear turtlenecks, mini skirts, flare and bootleg jeans, you can even wear "club-wear", but be careful to not get the really low necklines as to fear of exposing breast forms. However, I am experimenting with some make-up techniques so u can expose your breast forms but appear as real breasts. It can get expensive but well worth it. Since your young you might not find too many options on your budget. Find tasteful size breast forms proportionate to your shoulders and chest. There are a bunch in eBay, but be careful each cup size varies on the band size so check your chest circumference and I suggest oval shape plus 3M super 77 adhesive to put on breast forms( found at craft stores) and goo gone as adhesive remover which for both is like 15 dollars total compared to the 60 dollar primaries. As for hiding your "manhood" wear a Gaff, they run from 15-20 dollars. As for hair removal, get Revitol, yes it is expensive but for men who have thick hair follicles, and we all do have it ,this does the trick for like a month. Nair and veet just act like foamy razors. In your budget go eBay and buy breast forms(janetsclosetstore or stephaniesbosombuddies2009 I trust), revitol, Gaff, full wigs (please be tasteful) and Tamera pantyhose (if u have a tan or dark skinned) the reason for the hose is it is cheaper alternative to revitol, just shave your legs and wear them it hides the shaved hairs and razor bumps. Clothes and other stuff can be found at discount clothing stores and craft/hardware stores. This took years of trial and error but that is the way you learn and I am happy

  5. Lisa Kaufmann 28 October, 2010 at 08:04 Reply

    To all the fellow struggling "women" out there regarding of age, but especially those in the more earlier years of their life, hang in there, find a true friend to trust, and learn about yourself as you experiment in growing up.
    Like many others have already said, "It does get better." I grew up as a child of the 50's & 60's shortly after Christine Jorgenson came out. At least I then found out there were others who might be like me. A close buddy of mine at the time & I did some experimenting and I really found out who I wanted to be. He & I did do some boyfriend/girlfriend stuff for a while until he went off to college. Then I, like so many others, went back & hid in the closet only occassionally to venture out. Always on the look out for something that might give my inner most thoughts away. Now that I am much older and have grown more mature, I do know that "Yes, it does get better." So hang in there, be yourself and do not listen to others who only think they know.

  6. Chris 25 July, 2010 at 19:11 Reply

    On the topic of hiding, when I was in junior high and high school, I used the space below the bottom drawer of my night stand. That lasted quite some time until my older sister went into my room to look for something in my closet and used my nightstand for a stool. when she moved it, all my stuff was left in the middle of the floor.

    Today as I am older, I have two places – one for regular wear and one for special occasions. I don't go out in public so regular wear is stuff I wear in the car to and from work and/or under my clothes. I keep this stuff in the back of my masculine pick-up truck.

    Special occasion wear is what I pull out when my wife and kids are out of town. I keep this stuff in a cupboard in my masculine garage. I say this knowing how heurotic it sounds but justifying it all the same…:)

  7. Robert 24 January, 2010 at 09:56 Reply

    Todays youth has it easier with crossdressing then what I had to do as a boy. Except for dresses primarily, boys skirts are readily available to every male in America. Even in anime there are hundreds of sites that offer crossdressing boys. In 1961 , at 11 yrs of age, I started crossdressing. I did not have to sneak around. My mother thought that all boys should wear dresses. She dress myself as well as my two brothers. I took to them like a duck to water, my brothers did not. by the time I was 16 yrs of age I had a closet full of dresses and skirts.
    Although today most boys, according to two different websites, will in fact wear them, they don’t know how to wear them properly. The boys usually wind up exposing themselves (under garments) or wear their shorts under them. If boys are going to wear dresses or skirts then mothers, sisters and girlfriends need to teach them. Dresses require slips and panties, not shorts and tighty-whiteys. Skirts sometimes require halfslips as well. Boys need to be taught how to wear and put on bras too.

    • Geena 14 December, 2010 at 03:50 Reply

      You bet, sweetie! I have been wearing bras, garters and panties since I’m fourteen, and actually learned at six. My size is 36-B and even if for many years I felt guilty about it, nowadays I wear a bra and a panty virtually every day of the year, and got myself the hell of a collection. You never feel more feminine than when you see yourself in a beautiful lace underwear. I say, long live Wonderbra! God save Victoria’s Secret!

  8. Emily 22 January, 2010 at 12:37 Reply

    I’m quite lucky, having started cross dressing when I was 17, however due to doing my computer studies which occupied most of the time, I’d put it on the ‘back burner’ so to speak, do I regret it? no not at all because their was other things that I was doing, like going out with friends and enjoying being young. I’d figured back then that you’re only young once and that their was plenty of time to dress when I wasn’t out and about. (was still in the closet then).
    The other thing I realized was the importance of having a good circle of friends you can trust.

    Now I’m 24 years old, having well and truly finished my studies and in work. I still enjoy what I was doing in my late teens but also spend more time dressed, since coming out of the closet it’s made life that little bit more easier and ultimately more fulfilling.

  9. Ronnie 22 January, 2010 at 06:31 Reply

    Yes, I also wish I would have dressed as the girl I was as a teenager,but I/we can not go back.
    Lets all look foward in what ever “stage” we are in. Lets laugh,sing,dance,wear heels (LOL) and be happy… it’s about time.

    God bless, Ronnie

  10. gail 21 January, 2010 at 20:06 Reply

    One of my biggest regrets is never cross dressing as a teenager.
    I distinctly remember, as a 12 or 13 year old, wondering what I would look like as a girl, and of being told by young girls that with my slight frame, bright blue eyes, and long eye lashes looked like one.
    I had two girl friends around this time spending lots of time with them, and more then once they offered, or maybe threatened, to give me what would now amount to a transformation. I think they meant it as dig, or possibly even an insult but, they were also quite serious about it, and although outwardly embarrassed, inwardly I was always flattered.
    They never did “transform” me. I wish they would have.
    Looking back I can’t help thinking it would have brought my desires into sharper focus, and helped me see a clearer picture of myself, perhaps saving many wasted years.
    Not to mention I miss having a physical picture to combine with the mental picture I have of myself as a young girl.

  11. Ragina 20 January, 2010 at 11:44 Reply

    So true,so true. How I wish that there was someone to guide me along the way when I first figured out that I was a crossdresser. Now we who have been there MUST help the ones who are now just begining to realize themselves. To all our young sisters, please do all you can to learn about being transgendered. This is a wonderful place to begin. I’m sure that if you post on any comment here, you will find someone to talk with and help you. Most of all, dear ones, love yourselves first. That is the most important thing. Next, find a person that you can trust completly to help you along. Don’t let ANYONE tell you that you are wrong, that you are sick or a pervert, or any such thing, because it’s not true. You are a person of worth and value. Just because you present yourself in a different wrapper than what others expect, does not make you a bad person. Trust your heart, and your faith and then be beautiful as you are.
    Love to all, Ragina

  12. Ronnie 20 January, 2010 at 06:29 Reply

    Vicki, you are right we need to listen if when we do not have answers.
    I wish I would have someone to listen to me when I was young.
    I also feel very much like a teenager now that I’m honest with my self and starting to live my life more openly. I have been blessed with a very supportive wife.
    The “tg” community needs to be more visible with positive role models
    so lets be our selfs (as much as our “lifes” allows us to be) and beautiful girls and woman.
    Stay safe,stay pretty, God bless… Ronnie

  13. Vicki 19 January, 2010 at 20:30 Reply

    This is not so much for the teenagers out there as it is for us girls who have walked this path already. If you are like me, there was no one to go to when I was a young adolescent grappling with these mysteries. Vanessa, I agree, this is a tricky area to get into. But the least we can do is be there just to listen, to empathize where the stories intersect, to know when to admit we don’t have answers when we don’t.
    I feel at times at 54, I am still a “teenager” when it comes to emerging as my true self. My skin just sags a little more, but in a sense so many of us are new to the possibilities. Still, there has to be a time when TG comes to a more full acceptance and understanding for the general populace. Maybe we can walk with these youngsters out a little bit more, being positive and affirming role models for them, just by being willing to risk ourselves. How can they know it will turn out ok, unless we show them that, yes it CAN turn out ok, and here I’m living proof.

  14. Ronnie 19 January, 2010 at 18:45 Reply

    My teenage sister, the advise that I can give is that be true to your self.
    The feeling of “cross dressing” or in my case of being a girl/woman will most likely never leave you. I know this to be true for me. I’m 44 years old now and ONLY in the last few months been true , honest with my self,that is to say come to terms the I’ve been a woman all of my life.

    If I would have had the resources like the internet I beleave I would have come out to my self first anf then my parents. I have been “dressing” has my true self in one way or another since I was 7-8 years old. I would hide clothes and shoes (which I love) behind my dresser (which I moved into my closet…much safer that way) my mother never found my clothes. She did find some nail polish and a pair of panties. She later told me that she thought it belonged to a girlfriend. I just came out to my mom right before Christmas.

    One very important thing is,don’t think because you feel female or simply enjoy wearing female clothing that you are gay.
    I had many male sexual partners in my younger years. Looking back now it was not because I was gay, but rather because I was trying to find someone who would like my fem side and that my teenage sister is very dangerous.
    I’m now happy and married to a very loving and supportive wife.I now understand more than ever that I identify as a woman but never emotionally connected with a man. I love woman,but yes I’m a woman.
    That is not to say there is anything wrong with being gay but PLEASE take your time. Make one special freind that you can share your feelings with and build trust. Be honest with your self and find the right moment to share thoughts and desires with your mom or dad or both.

    Stay safe,stay pretty…and if at all possible think in pink… LOL
    God bless… Ronnie
    ps..
    just came back from shopping wearing my new heels and outfit..wow what a great feeling to be me!!

  15. Lynn Jones 19 January, 2010 at 13:40 Reply

    practice and get her feedback

    Practice, practice, pracice :) Magazines – and obviously – the Internet are great sources of information.

    If I may, I’d like to add something about judgement. :) Don’t judge yourself too harshly and try to avoid comparing yourself to those airbrushed faux women you see in the media. Most women I know, don’t look like that and neither do most of us trannys either. :)

    I know it’s tough and confusing, but try to think about the good stuff you have going on. Try not to worry about the future – if you think you are CD – so much, it’s funny in that lots of things kinda take care of themselves as you get older.

  16. MELONY 19 January, 2010 at 08:40 Reply

    When i was younger {12} i put on my mothers makeup sometimes, to experiment, even though she would put it on me for dance recitals, and i learned from her to use noxema skin cream that always seemed to work to remove makeup, hugs melony..

  17. Geena 13 December, 2010 at 20:50 Reply

    You bet, sweetie! I have been wearing bras, garters and panties since I’m fourteen, and actually learned at six. My size is 36-B and even if for many years I felt guilty about it, nowadays I wear a bra and a panty virtually every day of the year, and got myself the hell of a collection. You never feel more feminine than when you see yourself in a beautiful lace underwear. I say, long live Wonderbra! God save Victoria’s Secret!

  18. Geena 13 December, 2010 at 20:50 Reply

    You bet, sweetie! I have been wearing bras, garters and panties since I’m fourteen, and actually learned at six. My size is 36-B and even if for many years I felt guilty about it, nowadays I wear a bra and a panty virtually every day of the year, and got myself the hell of a collection. You never feel more feminine than when you see yourself in a beautiful lace underwear. I say, long live Wonderbra! God save Victoria’s Secret!

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