One small step for man — one giant leap for personkind. Crossdressing first steps.

I was chatting with a friend of mine the other day. We were discussing how hard it is to take those first few steps outside as a crossdresser.

The circumstances of these first few steps are always daunting. Regardless of whether these are taken in the confines of a drag club or stepping out into an unfamiliar environment they are likely to be a few steps that are never forgotten. But is there any way we can make it easier? And should we?

Well, remember what this process is. It’s the commitment to being someone that you’ve likely denied for many years. This is a dramatic emergence of the person that has been hidden for most of your life. It’s hardly surprising that such a process is as frightening as it is. In a sense, having the courage to make those first tentative steps is an essential part of the growth into the person that you are going to be ever after. Just as birth is accompanied by pain — in some small way, so is this stage in life. The commitment and courage required to own this and step forward is certainly something that not everyone is ready for. However, once there the drive to do so becomes quite powerful.

I generally suggest that one of the best ways to take those first few steps is to do so with a close female friend. That masculine part of us always gains power from being with a beautiful woman. I personally found enormous comfort in my first few steps being taken beside a woman of extraordinary beauty. Whatever people looking at you may think, if you’re with the most stunning person in the room they’re going to wish they were you. Before long, being myself became very much easier. However, I won’t ever forget the kindness of my companion who helped me take those initial tentative steps. I have no doubt her presence made things much easier.

Later, while traveling, I found it easy to present myself to the world as I truly am in the knowledge that far from home I was unlikely to bump into anyone I know. I gradually became more comfortable with my presentation and eventually it became very easy. The fact that I eased into it while travelling seemed to make everything much easier. Being in a neutral environment was certainly beneficial.

Going to a drag club is a wonderful way to get comfortable with the idea of dressing. Most drag clubs not only welcome crossdressers, they realise that people in the bar enjoy the presence of people who crossdress. This can lead to the drag club being a very comfortable place for people like us. You’re likely going to find a level of acceptance that is quite surprising. Certainly, that’s been my experience. It’s hard for people to be excessively judgemental in such an environment.

Another venue that can be a great way to take that first step is on holiday. Our own conference is a great four day experience in which one can enjoy safe first time dressing experiences. With workshops and activities, our guests can choose whether they wish to dress or not at any given time — and how far to go with it when they do dress. The same can be said of Jennifer’s cruises with

Either way, however you choose to do it, this is a step you’re going to need to take one day. Do it with planning and do it with confidence. Feel free to email me about it if you need to.




Holding a mirror up to the world, and then applying a rather fetching shade of lipstick. The crossdressing blog you’ll love!