Activities to do as a crossdresser to feel more comfortable as a woman

When you first begin your crossdressing journey, you may not feel comfortable as a woman. Deep down you know that you want to be, but years of societal gender role conditioning has now made it impossible for you to feel comfortable with your feminine side without it feeling ‘wrong’ in some way.

Do not worry, you are not alone. This feeling of fear or lack of self-confidence is very common for beginner crossdresser as it feels very unnatural and almost impossible to feel comfortable as a woman.

If all of that sounds like you, you have come to the right place. You currently need advice from someone who can guide you through things to do that will help you get over this fear that you are feeling with simple yet effective activities that will make you feel comfortable as a woman in no time!

Some of these may require you to step out of your comfort zone. But that is the only place where you will finally become the woman you want to be.

So, without further ado, let’s dive right into 5 things that you can do to start feeling comfortable as a woman when you are crossdressing.

Have a photo shoot in your best feminine attire as a crossdresser

Something that can be quite enjoyable and relaxing is organising a self-photo shoot. If you have introverted tendencies. This is a great way to build some confidence in you by getting dressed up and dolled up by yourself and seeing how beautiful you are or how beautiful you can look as a woman.

What’s amazing is the freedom that you get to experience doing this on your own. Without having to worry about others judging you, you can spend a whole day of just practice putting on makeup with different outfits until you find a few looks that give you the most confidence. You will end that session feeling a bit better about yourself and begin to truly realise the unexplored possibilities.

 If you are a bit more extroverted, have friends that are more supportive, or have friends that are into the same thing, feel free to reach out to them to come and take photos for you. This way you get to bounce ideas off each other and find out what works for you and what doesn’t. You can also organize costume parties with your friends, which we will cover later.

Join online streaming platforms

An emerging trend in the crossdressing community is to get involved in the streaming industry. Several crossdresser women get a thrill by dressing up as a woman and live streaming themselves either playing games or just simply talking to people.

While the internet can be an unpleasant place for anyone, it also has fantastic communities whose support you can enjoy. There are several YouTubers and live streamers on platforms such as Twitch where crossdresser have built a large following of supporters. These are the perfect groups of people that you should associate with as you already know they support the crossdressing community.

The added benefit to having an online streaming account is you get to see live reactions of people when they see you in your feminine alter ego. You might find that several guys online actually find you attractive. That might give you the confidence-booster you need to go out to the real world as a beautiful woman.

If you have experiences and advice that you’d like to share with others that are on their crossdressing journey, a genuine option for you to consider is creating a YouTube account where you share your stories. When viewed by the right audience, you can inspire several others that are yet to go through what you have.

Host a few costume parties

If you are part of a group of other crossdresser women or would like to get to know others that crossdress. Hosting a party might be the best way to go. Social gatherings and alcohol help to relax everyone’s nerves which will allow you to bring out the woman in you with higher confidence than in any other setting.

It doesn’t even have to be with other crossdresser women. If you have a good group of friends that has supported you in your crossdressing journey, invite them over and make a party out of it. Make it a ‘coming out party or a makeup party or a cosplay themed party – any party that will allow you to get dressed up.

The best time to have a costume party is during themed holidays. Halloween is a very popular event for everyone to get dressed up but that doesn’t have to be the only dress up holiday you take advantage of.

You are now ready to walk outside

Once you’ve had your fun indoors with hosting parties and streaming and hosting photo shoots by yourself and with your friends. The next step to take to feel more comfortable as a woman when crossdressing is by simply going for a walk.

This does take some courage, but by doing all the other stuff we mentioned above, you should feel a bit more comfortable in dressing up. Use this confidence and step out to finally enjoy what it feels like to freely share your inner woman with the world outside.

It is essential to keep it simple, however. Keep to yourself and don’t go to draw attention or strike a conversation or do anything that might draw too much attention to yourself if you don’t want it. If you do have an unpleasant experience the first time you step outside, that will backtrack all the progress you would have made so far.


When you first start crossdressing, you won’t easily feel comfortable as a woman. Because it is something utterly foreign to anything else you have done up until this point. Therefore, it is vital that you take these early steps carefully to ensure you do not have a negative experience at a time when you are not mentally equipped to handle it.

Follow all the advice we have given you in this article and you will be much better off than most beginner crossdresser women out there. You have an amazing journey of self-discovery ahead of you – make sure to enjoy every minute of it!

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