There are many ‘first times’ when we crossdress. One of the most challenging is the first time we go out in public. Like so many things, this is best approached with a good plan, and in as controlled a situation as possible.
I am going to describe this as it worked best for me, and of course there is no particular right or wrong way to manage it. There are probably as many ways as there are corssdressers. I feel particularly fortunate that my own experience was fortunate enough to have been a very positive one, and one that may be a good template for others to follow.
Having a good collaborator is a great idea. By the time you decide you’d like ot go out in public you are likely to have dressed with someone more than once. This means you’ll have some idea of a few people in your life who are good allies in this respect. Personally, I am not a great fan of paid dressers – often a relationship that is not really based on trust, however for some people this is a perfectly reasonable alternative. Make no mistake, there are some paid dressers who are valuable and professional.
Generally I suggest people learn the skills offered in my Premium Program, around recognizing and engaging with a person who wishes to share your crossdressing with you. This is doubly important when going out into a public space, because you want to feel a sense of sharing the experience and participating together in the venture. It can be both the most frightening and wonderful experience for a crossdresser. And, of course, you only get one first time.
With all this in mind, you might want to be as prepared as possible. I found myself in a place that was very liberal and open to ‘queer’ behavior, so when I jumped in I was doubtless more nervous about it than anybody else. As I stepped into a wine bar and crossed the floor all eyes seemed to be on me. Thousands of them. Well, there were only four or five people in the room but it felt like thousands.
It was a safe environment, and as it happened I was with the most beautiful woman in the room, by far. That’s always a great help. If your collaborator happens to be drop dead gorgeous you are off on a winning footing. Additionally, the particular venue was very relaxed. In my case it was a hotel bar, with few people and a very relaxed atmosphere. I sat with my back to most of the patrons and felt quite terrified. Regardless, I also felt quite beautiful, thanks to the encouragement of my wonderful collaborator.
If one were to analyse why it was a successful situation, it’s partly because of the person I was with, partly the location, and partly the fact that being a hotel I was relatively anonymous. If you’re going to do this, travelling away for the weekend and choosing a location you’re comfortable with, clothes that look great and having plenty of time to prepare, are all factors that will help you.
Another alternative, and one that can be very successful is to choose a venue in which you are not the oddball. Going to a drag club, getting a sense of what the atmosphere and environment are like, and then returning the following night dressed, is a great idea. Again, traveling for a weekend getaway is a great way to do this. Drag clubs are great fun, and you can quickly get an idea of how far you want to go if you’re going to go dressed. Getting a sense of the place without dressing is something no one is going to criticize you for. Generally, you’re going to find that a drag club will be pleased to have your business and be pretty non-judgemental. Everyone is just having a bit of fun.
You can have a drink, relax and may even get to see some wonderful performers.
To come back dressed, either fully or partially the next night is really not going to be a problem. You’ll feel safe and know what to expect. Again, working with a partner or collaborator is a great idea. I have been amazed by how many women love to hang out with crossdressing men. Asking a trusted friend to come with you is not as hard as you may think.
Keep this in mind. No one expects you to be completely passable. It’s unlikely you will be the first time you go out, unless you are exceptionally lucky. Regardless, crossdressing is like many things. The longer you do it, the better you become at it.
Keeping it as simple as possible and not worrying too much about being flawless is simply a good idea. Many crossdressers will never pass. It doesn’t matter. Your goal should be to feel great – to feel like yourself. At first it’s going to be frightening, however If you can get past that, you’re doing wonderfully.
Let me know how you get along.