Crossdressing Teens: 21 Tips for Teens & Parents (2023)

Crossdressing teens are more common than you may think.

Crossdressing Teens

However, the desire for a young boy or girl to cross-dress can bring a lot of harm to their mental health, if parents don’t react favorably or if the teens themselves aren’t prepared for the backlash they may receive.

That’s why I was so keen to write this post containing 21 tips for crossdressing teens and their parents. 

So, let’s dive in. 

Cross Dressing: Advice For Teens

Here is my most important advice for teenage boys and girls who are interested in cross-dressing. 

1. Is It Normal To Cross-Dress?

It depends on your definition of “normal”.

It’s probably not one of the top 10 most popular hobbies for teenagers, but there are plenty of reasonably-sized crossdressing communities across the world, and many adult crossdressers began this habit as adolescents.

As a teenage boy or girl, you’re susceptible to want to partake in activities that are “normal” or popular”.

However, I promise you that this isn’t as important as doing things that make you happy. 

This is a wonderful life lesson that you’ll learn if you continue crossdressing. 

Once you understand this lesson, you’ll realize that it doesn’t matter whether crossdressing is considered “normal” or not. 

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2. There’s No Better Time To Be Courageous Than Now

It does sometimes take some courage to embrace when you have a niche hobby, especially in your teenage years when you’re typically very concerned with what people think about you.

This is especially true with activities or a lifestyle that involve portraying a different gender identity or sexuality than what you previously expected.

However, I would like you to know that most people who enjoy these types of activities eventually find the courage to embrace it without filters. 

Once they do, they feel a lot better. They feel a sense of freedom in their life that was missing when they kept it a secret. 

Many people who enjoy crossdressing have admitted that they regret not embracing it sooner. 

With that in mind, the best time to be courageous about your hobby is now.  

3. Your Teenage Years Are The Best Years To Try New Things 

This is a period of self-discovery. These are the best years to experiment with new ideas for what you do and don’t enjoy in your life.

4. Crossdressing Isn’t Necessarily A Sign That You’re Gay

There is no direct link between crossdressing and being gay. There are plenty of straight crossdressers. You might not want to change your gender identity either. 

Of course, if you do think you might be gay, there’s nothing wrong with that either.

5. Crossdressing Doesn’t Mean You Want To Be Transsexual

There are plenty of crossdressers who feel perfectly comfortable in their bodies. They simply enjoy wearing the clothing of the opposite sex.

6. It Might Shock People When You Reveal You’re Cross-Dressing

It can be a shocking revelation to hear from a friend or a family member. They might react with extreme emotion. This is especially true about other children, who might not have as much knowledge about crossdressing as adults. 

That doesn’t mean they don’t love you or don’t want to be your friend.

In most cases, they’ll calm down over time. 

7. It Might Shock Them Even More If They Catch You 

If someone spots you crossdressing before you reveal that you like to crossdress, this can trigger an emotional reaction because it is somewhat shocking to see.

Your parents might get upset for keeping this as a secret from them, especially if you’ve been borrowing clothes from their closet. 

It’s usually best to tell your parents that you like crossdressing as soon as you’re comfortable. 

8. It’s Normal To Be Afraid To Talk About Cross-Dressing 

There’s nothing wrong with cross-dressing.

However, it’s normal to be afraid to talk about it with your friends and family about it, because you don’t know how other people will react.   

9. If A Family Member Doesn’t Approve Of Your Crossdressing, It Doesn’t Mean They Don’t Love You

There’s still a lot of ignorance about crossdressing – and it could be that your family isn’t aware of how harmless and innocent it is.

If they react adversely, it could be due to their lack of knowledge. It certainly doesn’t mean they don’t love you.  

10. Be Loud And Proud

It’s not easy to be loud and proud about your niche hobbies, especially in your teenage years when you’re still discovering who you really are.

Still, I would urge you to do your best to be confident about your decisions.

People are more likely to accept your hobby when they see how proud you are of it.

Teenage bullies are less likely to target you when they don’t see any signs of insecurity to poke at. 

If you’re still in the initial stages of discovering your fashion sense, you can be loud and proud about the fact that you’re trying to figure out whether you like this thing or not. 

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11. Connect With Other Cross-Dressers Online

Crossdressing is a niche pastime, so you might struggle to find people who are supportive of it. Luckily, with the power of the internet, it’s easier than ever to connect digitally with people who have the same niche hobby as you. 

So, go ahead and connect with other cross-dressers on the internet. This can do a lot to help you to embrace your new hobby.

12. Want Someone To Talk To About Your Crossdressing?

If you don’t feel comfortable talking with your parents about your desire to crossdress, perhaps you’d prefer more comfortable talking with a Life Coach for Teens.

Life coaching isn’t for teenagers who are bad or messed up. These professionals can help teenage boys and girls to make more sense of their thoughts and to share their feelings in a confidential environment. You can learn more about it in my guide on Teenage Life Coaching

Crossdressing Teens: Advice For Parents

Here is my advice for mothers and fathers of boys or girls interested in wearing clothes from the opposite gender. 

13. Why Does My Son Cross-Dress?

There might not be a particular reason that your boy likes to cross-dress, other than he finds it fun. It’s natural for young boys and girls to want to play and experiment with everything the world has to offer, and they tend to be more open-minded than adults.

Just because your boy likes to wear skirts and makeup, it’s not necessarily a sign he’s gay nor that he wants to be a female. There are plenty of male cross-dressers who are perfectly happy with what’s between their legs.  

There might not be anything specific that you’ve done to encourage this. 

It’s not always that deep. 

At a particularly young age, they might know anything about crossdressing and switching up gender roles, other than it’s fun. Maybe your son is trying to be like Mom, his sisters or his female friends.   

As a teenage boy, it could be still just a phase he gives up, like young boys and girls often do with other hobbies.

There’s nothing wrong with asking your little boy or girl why they like to crossdress, although you might get a simple answer like the one above. 

14. What Triggers Cross-Dressing?

There are no known ‘triggers’ for a boy or girl wanting to cross-dress, in the same way, there are no known triggers for them wanting to learn guitar.  

15. Love Your Child Unconditionally  

Perhaps you’ve read this guide about how harmless and innocent it is for children to wear different clothes around the house, but you still don’t want them to do it.

That’s your prerogative.

However, I would strongly urge you not to shame your child or withdraw love because of the clothes they want to wear. 

If you want your boy or girl to grow up with confidence and good mental health, you should love them unconditionally.

16. Forbidding Things Is Rarely Helpful

It’s up to you what rules you set in your house.

However, in most cases, it’s unhelpful for you to straight-up forbid things.

In most cases, this causes resentment with your child and encourages them to want to do it more.  

It’s better to explain to them why they’ll have to dress a certain way in certain places, like at school for example.

Give them a healthy limit out of love, the same way you might for video games or ice-cream.  

17. Times Are Changing

A few generations ago, it was essentially forbidden for girls to wear a t-shirt and jeans. Now, this is a completely normal part of women’s fashion. 

In recent years, we’ve recently seen relevant A-list rappers – supposed symbols of alpha-male masculinity – start dressing in skirts on stage. We’re seeing more male celebrities in makeup too.  

The clothing considered normal for either sex is changing all the time. Something to bear in mind.

18. Don’t Ignore Their Crossdressing Habit 

To show your little boy or girl that you love them, it’s essential that you show interest in their choice of clothing.

Talk to them about their feelings so they have a chance to explain why they like to wear the stuff they dress in. Play with them while they’re in their favorite clothes. Perhaps you could even help to search for new stuff to wear

Ask how they think their brothers and sisters feel about their clothing. Ask if the other boys and girls at school know about it.

These are supportive questions that will allow you to check up on your child and understand the best way to support them. 

19. Is Cross-Dressing Addictive?

It’s not chemically addictive in the same way as cigarettes or alcohol. Perhaps they’ll enjoy it so much that they don’t want to stop, the same way they might feel about playing video games or softball.

20. Delay Permanent Decisions Until They’re An Adult

Your boy or girl might express desires about wanting to be male or female. 

Yes, little boys and girls can say the darndest things at a young age, but please don’t shame them when they express such thoughts.

The most important feedback to give a child is that you’ll still love them no matter what gender identity they choose or what they’re wearing. That’s assuming you want a mentally stable child.  

With that said, these aren’t the sorts of decisions that should be made while their body is still developing during puberty. Let their bodies fully develop first. 

21. Don’t Hesitate To Seek Advice 

If you’re struggling to deal with the fact that your little boy or girl cross-dresses, don’t hesitate to seek advice from a counselor or therapist yourself. Counseling services can help you organize your thoughts and give you an unbiased review of your situation and how to change it for the good of your family.

It’s fine to seek professional help to deal with any family or relationship situation you’re struggling with.  

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Any Questions About Cross-Dressing Teens?

Thanks for reading my post. I hope you found the advice useful as far as what to do when your teenage boy or girl cross-dresses.

Please note that this advice is based on my studies of parent-child relationships and isn’t intended to offend anyone.