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.