How Can Crossdressers Enjoy Their First Travel While Crossdressing

Traveling and crossdressing at the same time is something most of us dream of doing. After all, wouldn’t it be amazing to enjoy a relaxing vacation while expressing our feminine side? Without a doubt, it would. Then why isn’t it a common thing to see a crossdresser enjoying a trip? Well, there are a few reasons for it. First, a good portion of our sisters have a lack of confidence or are afraid they won’t pass. Second, some of them aren’t able to come up with a travel plan or even an itinerary. Last, but not least, some others don’t know what to do on the trip while dressed up en femme.

With that in mind, my plan is to provide you with enough information to ensure you have an awesome first trip as a girl. To do so, you have to understand how to prepare for a trip by paying attention to the details and setting your priorities straight. It’s also useful to practice certain aspects of crossdressing and set up your travel outfits. Knowing yourself is as important as knowing your destination, and both things will influence how much you enjoy your trip.

So, now that you know what you have to do, I must tell you how. In order to ensure you enjoy your crossdressing trip, I’ll develop each concept in-depth and give some extra tips. My intent is to cover the whole traveling process, from the planning, the travel itself and the return home. Even though this is a broad subject, I’ll give as many details as possible.

1. Research about your destination

Where do you want to travel to? What would your ideal trip look like? How would a crossdresser be received by the locals there? These are the three most important questions you must ask yourself when you research your destination. Generally, the first one depends on the other two. What you want to do is to conciliate safety with enjoyable activities, which may vary from one crossdresser to another. For now, let us focus on the middle question.

Take your time to think about what you like to do while traveling, and what kind of establishments you want to visit. Ask yourself: What is the main goal of leaving your city? Is it to visit a beautiful place? To go shopping for stuff that usually isn’t available near you? Or, perhaps, to try out local cuisine? The answer to this will determine the type of destination you should pick, and you can think better about the rest based on that.

The next thing on the list is to find a place where crossdressers are well-received. My experience tells me that large urban centers are more welcoming to us than countryside towns or small provinces. Even though you can use that as general guidelines, remember that each country has its own culture. Each one with different demographics and popular opinions. After finding out about a few locations that match your requirements and are safe for crossdressers, you can decide based on ratings.

A good way to do that is by using Tripadvisor, or any other tool that compares ratings between locations, hotels and other stuff. This way you can have an overview and make a better choice. After that, you’ll have to find a safe place to stay and finish your itinerary by choosing activities and places to go. The idea is to organize your time to get the most out of your trip, but I’ll talk about it later.

2. Practice your endurance

If you’re traveling as a crossdresser, you’ll have to be prepared to endure your own outfits for a while. For example, If you are dressed up in a plane or in a bus, you won’t be able to change into your male clothes and remove your makeup. Let alone remove your shapewear, even if you feel a degree of discomfort. The same thing is true if you’re at a beach, a restaurant or any tourist attraction. My point is that if you want to travel and spend your trip dressed up, you’ll have to be prepared. You’ll have limited opportunities to change your outfit.

One of the main causes of discomfort is the lack of endurance. It happens more often in people wearing more restrictive outfits and compressive shapewear. To avoid this kind of situation, you must practice your endurance, or adapt your outfit to be more comfortable. Try to practice for a couple of months before you start planning your trip, so you can make sure you are well prepared. Try out different types of shapewear, methods of tucking and different outfits. Do so until you find something comfortable that you like. To increase your resistance and endurance, wear your shapewear for at least a couple of hours every day, and exercise if possible. Cardio is the best choice since it improves your breathing and doesn’t develop your masculine features such as muscles.

Another piece of advice is to drink as much water as possible. The compression of the shapewear may cause you to sweat, so it’s good to have a water bottle handy. The downside is that you may need to go to the bathroom more often, so make sure you choose an outfit that allows you to do so. It’s useful to check out the local bathroom policy, but if you’re in doubt, it’s up to how well you pass. If you pass too well as a woman, go to the lady’s bathroom, but if people can clock you and tell you’re a crossdresser, you may use the gentlemen’s.

Remember to rest every once in a while, as it helps you to increase your endurance for when you need it. Even if you want to crossdress full time on your trip, remember to at least take off your shapewear at the hotel, so you can breathe. This way, you won’t get exhausted too quickly and will be able to enjoy your time outside as much as possible. It’s all a matter of balance, as most things related to crossdressing are.

3. Stay at a safe place

Choosing the right place to stay is more important than it seems at first. Of course, you may want to stay in a place that is close to where you want to go, but comfort is also important. Not only that, but you also need a certain degree of privacy, at least enough to dress up and do your makeup in peace. The idea is to stay at a place you can use as a safe room, where you can go to change clothes if you need, and safely store your crossdressing stuff.

This is even more important in countries that are less open to crossdressing. When searching for a place to stay, try to discover how well those places welcome LGBTQ+ people, and how much privacy they offer. Discretion may be crucial in some cases, and that’s why I like to reinforce the importance of researching both your destination and your stay. Once you manage to do that, you can rest, since what’s left of the planning is considerably easier.

4. Avoid overloading yourself

Pick your priorities to avoid getting overwhelmed, is what I say to anyone planning a trip. This advice is twice as valuable for crossdressers though. You must pay attention not only to how many things you want to do but also to how many outfits you take with you. If you plan a lot of things to do, you may not be able to attend to all of them, which may leave you upset. Also, if you bring too many different outfits, chances are that you get undecided on what to wear, and waste precious time trying to figure it out. Besides that, you could risk overloading your luggage and having to pay extra fees depending on your method of travel.

I know sometimes we get over preoccupied and our anxiety tells us to do as much stuff as possible when the opportunity comes. But when we exaggerate, we risk not enjoying our trip at all due to the consequences. Good thing is that I know a few tricks to help you optimize your time and wardrobe. To be more precise, I can tell you how to choose what you really need to wear, and how to tell you what’s worth doing during your trip.

First, let’s talk about the outfits you may choose to take along with you. My trick is to figure out how many days you plan to stay and get one outfit for each day. I also like to include a couple more for backup, and an extra set of underwear. This shall be more than enough to fulfill your necessities, but not to overload your luggage. If you plan to stay more than a week and have means of doing your laundry, you may bring half as many outfits as you would. Limit your hairstyle to a single wig if possible, as it takes a lot of effort to store and take care of them. Shapewear, on the other hand, is rather easy to maintain, so you can take a few more options with you.

5. Get company if possible

Traveling alone may be fun, but the company makes everything better. Not only that, but you may find that a companion can be extra helpful, even more in your first time traveling crossdressed. A person to help you is a key to increasing your courage and improving your confidence. One of the things that can hold us back from doing that kind of stuff, is the feeling of being alone, without support. Once you feel like you can count on someone, you’re going to notice how easier even the simplest things become.

I know, a considerable amount of us don’t even have a relative that supports us, but it doesn’t mean you have to feel alone. Finding a supportive friend may not be easy either, but it’s surely possible. Try to know more about the LGBT community in your hometown, and see if you manage to befriend new people. Mutual support is one of our key characteristics because helping each other makes us strong. So, don’t be afraid to meet new people if you feel isolated or rejected, as it may also improve your self-esteem. Please, note that it’s still ok if you want to travel by yourself, but sharing your experience is wholesome and helpful.

6. Keep your papers close

Never leave your house without your documents! This is even more important if your destination is a foreign country. Your passport is required not only for you to enter another country, but to re-enter your home country as well. Out there, to avoid trouble, keep all your papers close, as they are all you have to prove your own identity. Now, another useful tip is to keep photos of yourself in both male and female outfits, with and without makeup. This is recommended to help you avoid suspicions of identity fraud if someone asks for your papers while you are en femme.

If possible, tell the hotel crew in advance about your intentions, and clarify that you are a crossdresser. Do this to avoid any possible confusion with your gender and your identity, and to ensure you get enough privacy during your stay. Another thing that may help, is to ask for the inclusion of your social name in your documents. This is optional, and may not be possible in every country (or at least easy to access).

7. Choose your outfits with wisdom

Remember the talk we had about choosing how many outfits you should bring to your trip? Well, now I want to talk about which kind they should be, according to the nature of your trip. A crucial tip here is to research the local customs and culture of your destination, so you can have an idea of what is appropriate to wear. Also think about the activities you want to take part in, and what would be better to wear for them.

For example, if you’re going to the beach, make sure to choose a bikini that allows you to tuck. You may also consider a silicone bodysuit to hide your shapewear seamlessly. If you want to attend parties, wear something sexy but not vulgar, maybe showing a bit of cleavage, and wear comfortable footwear so you can dance. If you want to know more about local cuisine, try something elegant so you can enter fine restaurants and feel at home. It’s all about adapting your outfit to the environment.

What you must bring nonetheless is, of course, something very comfortable for your sleep time. This way you can have a good night of rest, ensuring you have a lot of energy to get the most out of your trip.

8. Enjoy the trip

Leave your troubles behind, focus on the present. And most importantly, do not hold yourself back. Be the girl you’re supposed to be, and use this trip to express yourself in full potential. I also want to point out that it’s normal to feel afraid and out of place on your first trip as a crossdresser. But please, don’t let it drag you away from your dreams. Even if you decide not to leave the safety of the hotel, dress up there and use your time to enjoy your femininity. The key to enjoying your trip is to stop caring about what other people think. Passing as a woman or not doesn’t really matter. What does matter is to be true to yourself, and express your true nature? You’re unique, beautiful, and awesome, so don’t let anyone tell you otherwise.

To take things to another level, register everything you can! keep your phone charged, and take as many pictures as possible. I love posting pictures of my trips, even when I’m not crossdressed, so I have a memory to look at. My advice is for you to create a new Instagram or Facebook account, with an email using your crossdresser name. After that, add other crossdressers and LGBT supporters as friends, so you have some people to interact with you in a positive way.

9. Go home

Once your trip is over, and it’s time for you to return, grab a souvenir if possible. I love collecting them, so I have something even more special than pictures to remind me of what I’ve experienced. T-shirts and street art are classics, but they can be virtually anything you see and like, even a rock. Before boarding your flight or ride home, check once again your documents and revise your luggage, so you don’t leave anything behind. If you want to, it’s also a fulfilling experience to bring gifts for your loved ones.

As we’ve seen, it’s possible to travel and enjoy your trip as a crossdresser. All you have to do is to pick your priorities and plan everything you can before you go. Research can save your day if done properly and allow you to have the best experience possible. However, you shouldn’t worry too much about every detail, since the whole point of traveling is to have fun and relax. And in our case, of course, to be the woman we always wanted to be.