How To Tell Your Parents You Crossdress – Step By Step Guide

Telling parents you crossdress is a big step. This ‘How to tell your parents you crossdress’ guide helps you plan a calm, safe conversation: choose the right moment, prepare what you’ll say, set boundaries, and share why dressing matters to you. You can go slowly, answer questions, and take breaks, your pace, your safety.

How To Tell Your Parents You Crossdress

For many, telling their mum and dad that they’re secretly crossdressing can be a difficult subject. You may already feel certain that the people closest to you will respond positively and show their support, but often that doesn’t make it any less easy to approach. But the fact is, being a crossdresser is a huge part of your life, and for many, dressing and feeling like a girl is who they are. Is this something you want to keep a secret forever? Probably not.

Thankfully, being a crossdresser these days is far less taboo than it once was and far more widely accepted. Clothing is becoming more gender-fluid and increasingly being seen as simply a form of expression. Even schools are now starting to allow boys to wear skirts under a new gender-neutral uniform policy.

If you’re wondering what’s the best way to tell your parents that you like to dress as a woman, then hopefully our tips and advice will help you make the leap.

♥ Surround yourself with like-minded individuals (confidence first) ♥

Although this doesn’t directly correlate with telling your mum and dad that you’re a crossdresser, feeling like you’re not the only person in the world who likes to wear female clothing can do wonders for your confidence. Thankfully, the invention of the internet means a group of crossdressers is only ever a few clicks away. You can find valuable info you can point your parents to, community and support over at Crossdressed UK.

To connect with other crossdressers, I prefer to use Instagram. There are countless profiles from individuals just like you who express an interest in crossdressing.

Try searching the hashtag #crossdresser, this currently produces 1.8 million results. Or search the hashtag #transgender which will give you 11.5 million posts to scroll through. These are accounts from real people who can follow, message, and connect with.

If Instagram is not your thing, then another platform I like to use is Reddit, particularly the subreddit r/crossdressing. This subreddit has 195 thousand members who you can ask questions and participate in discussions with.

Realizing how popular crossdressing is and knowing that there’s already such an enormous support bubble around you may give you the boost of confidence you need to make the first step towards telling your parents.

From my experience, many of the crossdressers on IG and Reddit are open to becoming your friend and having a little discussion with you. Most of them have been where you are today or are currently where you are now, and many will be happy to get to know you and have a conversation with you about it.

♥ Test The Water (what do they think?) ♥

Putting the feelers out and finding out what your parents think about crossdressing is step number one. By all means, you can simply ask them what their thoughts are about it but this may seem a little too bold or obvious, so maybe you could try a different tactic.

For example, you could pick a subject your parents are familiar with and talk about somebody in that field that is a crossdresser or has transitioned to a woman. Let’s say the topic is boxing, you could spark up a conversation about English boxing manager Frank Maloney and how he transitioned into Kellie Maloney, get their thoughts on the topic.

Another example could be the next time you’re watching TV and an advert for RuPaul’s Drag Race comes on, ask them what they think about men wearing women’s clothes and makeup. Do they respond positively or negatively? This could be the first step in telling them you like to crossdress.

If you do find you don’t get the response you were hoping for, then try to take this with a pinch of salt. Some people, particularly men/dads might just make a joke out of it. That doesn’t mean that they wouldn’t accept you wearing girls’ clothes. Unless they are incredibly bias they will almost always accept how you dress. You are their child after all and your style of clothing shouldn’t change their opinion of you.

♥ Wear Some Gender-Neutral Clothes (gentle exposure) ♥

Next, I advise that you slowly introduce your parents to seeing you wear women’s clothes. I’m not suggesting that you rock up one day kitted out in a skirt and pair of stockings, but maybe some form of clothing that could be described as gender-neutral.

Try wearing a loosely fitted girls t-shirt, or a pair of tight women’s jeans one day and see how they react. It may be that they don’t even notice. Or if they do, even better because you’re giving them their first insight into your crossdressing style.

As time goes on, you can do this more often. Then once you’re more comfortable and confident, you can start to become more elaborate by wearing more girly clothing and adding accessories like jewellery or some subtle makeup.

♥ Talk to mum first (choose a supportive first listener) ♥

By now your parents will have started to notice a change having seen you wearing more feminine clothes, so this is the stage to begin opening up. My advice is that you talk to your mother first. Mums tend to be more sympathetic than dads and having the backing of your mum can give you the feeling of security to tell your dad when you feel ready.

The next time you get some alone time with your mum, ask her to sit down with you and tell her you’ve got something important to talk to her about. The best way is to just come out with it and say something like, “mum, I don’t feel myself wearing boys’ clothes, I know that’s not who I am, I feel a lot more comfortable and confident wearing girls clothes”.

“Thanks for listening, this is important to me. I sometimes wear feminine clothes because it helps me feel more like myself. It isn’t about hurting anyone. I’m happy to answer questions, but I’d like us to go at a gentle pace. If you need time, that’s okay.”

Once it’s out in the open you can discuss your identity with her, explain to her that it’s still you, and give your reasons for wanting to dress in women’s clothing.

If a face-to-face feels too hard, send a message first:
“Hey Mum, there’s something important I want to share. Sometimes I wear feminine clothes because it helps me feel like myself. I’d love to talk when you’re ready. I’m okay to go slowly and answer questions.”

Highlight the reasons for how it makes you feel, the benefits you get from it, how you’re able to express yourself, and how it makes you feel confident in your own body. Then explain why you don’t feel this way in boys’ clothing.

Be specific about what gender you identify with. Would you describe yourself as transgender, gender-neutral, gender fluid, non-binary, a male that likes to feel like a girl, or simply somebody who prefers the look and feel of girls’ clothing? Do you want to dress as a woman all the time or just sometimes? Make sure you explain your gender and identity clearly with your mum so she can better understand you.

Your mum loves you no matter what and all she wants is the best for you, and seeing you happy means more to her than anything else in the world. If that means wearing female clothing then she will have no issues with that whatsoever.

Once she knows your secret you could ask her to take you shopping to get a few new items of clothing. This could even be a great way for you and your mum to bond and enjoy a new hobby together.

Once you’ve got your mum behind you, approaching your dad, sisters, and brothers should feel less stressful. Just repeat to them what you told mum only this time with your mum by your side for support.

♥ Final note (follow-up & next steps) ♥

Once your family knows your secret and you have their support, you should feel a huge weight lifted off your shoulders. You are free now, should you want to, to tell others such as your friends and extended family.

If your friends don’t support you and accept you, then you can feel safe knowing that those who matter most do you have given their full support. And hopefully, by now you’ve made many new cross-dressing and trans friends on social media so you’ll never be without a buddy to reach out to.

Tiffany Hart Lingerie would like to take the time to thank you for reading this article. I know that telling your parents you’re a crossdresser can be one of the hardest things you can do but I hope the tips and advice will help you make the first steps.

Please feel free to leave your comments in the comment section below and I will try to answer you as best I can.

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