A Teenage Crossdresser

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Teenagers and Crossdressing - too much confusion?

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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About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

24 Enlightened Replies

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  1. Robert says:

    Sorry I forgot to click follow-ups

  2. Chris says:

    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…:)

  3. Lisa Kaufmann says:

    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.

  4. rya says:

    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 says:

      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. CATCHERSTAR15 says:

    i have just came out, being a crossdresser and also being gay

  6. CATCHERSTAR15 says:

    i have just came out, being a crossdresser and also being gay

  7. unkown says:

    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.

  8. Jesse says:

    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

  9. I do believe all the ideas you have presented on your
    post. They are very convincing and will definitely work.
    Nonetheless, the posts are too quick for beginners. May you please extend them a little
    from next time? Thank you for the post.

  10. Geena says:

    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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