Novice Crossdressers First Time Shopping Guide

Any store that sells women’s clothes can be a paradise for crossdressers. We see a lot of items and outfits, and almost immediately start to think about how we would look in them. It’s a common feeling that’s quite hard to resist. What I know is that it gives me a lot of gender euphoria, and it’s very pleasant to walk out of said stores with a new outfit. However, some of us haven’t been able to try it out yet, due to a lack of confidence.

If that’s your case, fear no more. I want to encourage you to embrace it and experience one of the most exciting parts of being a crossdresser. First timers might experience a few challenges or fears, but I know how you can overcome most of them. Enlisting a friend to help you, going there crossdressed or even coming up with an excuse are common ways, but it doesn’t end there. Practicing your confidence and exercising your conversation are also great methods.

With that said, I must add that the effectiveness of each method may vary from person to person. In this article, I want to develop each technique in depth, so you can decide which one suits you better. I’ll try to make them as clear as possible, and point out the advantages and disadvantages of each one.

1. Asking a female friend for help

If you have confidence problems, and feel that you won’t be able to overcome them enough to go alone, enlist the help of a friend. That will work even better if said friend is a female or a more experienced crossdresser. A female friend will make it easier for you to browse through women’s clothes without raising suspicion, since you’ll be in the company of a girl. An experienced crossdresser, on the other hand, will boost your confidence and teach you their own techniques.

This one method is the same one I used. The very first time I went out to buy myself some feminine outfits, my girlfriend was with me. She helped me to browse the store and choose what to buy. She carried the clothes herself, so it would look like she was the one buying them. It was very effective, and no one suspected a thing. I still use this method sometimes, and it never fails me.

The advantages are that beginner crossdressers can do that without too much effort, and the fact that it’s quite effective. The downside is that you’ll have to come out to someone so you can get them to help you.

2. About crossdressing at the store

This method really varies between situations, as does its efficiency. It demands a bit more confidence, depending on how well you pass as a woman, and requires some practice. However, once you manage to master a few skills, you’ll be able to enter any women’s clothing store unbothered.

Before you do that, you’ll have to consider a few things. How well does your country treat crossdressers? How well do you pass as a woman? For how long can you endure crossdressing outside? If your county’s people have a poor opinion about crossdressing, it may be risky to do so in public, so it would be wise to avoid it.

You also need to consider how well you pass, to determine how much confidence you´ll need. Let me explain it better. If you pass as a girl, no one will even notice that you’re a crossdresser. Thus, you’ll be able to enter and browse the store like any other woman, and that demands less confidence. On the other hand, if it’s clear that you are a crossdresser, you might get some stares a certain degree of discrimination. It takes more confidence to endure that.

If you plan to do that, you’ll need a couple of female outfits. Do get a few before you go to a store, order them online. Once they arrive, try them and practice your makeup skills. Get used to how they feel and look on you, to increase your confidence. After that, you’ll be almost ready to crossdress and go to the store.

Another one of my tips for this method is about practicing. That’s because it will have a direct influence on how well you pass, and thus, on whether you may or may not choose this technique. Remember that passing isn’t just about your appearance: Your voice and your body language are also very important aspects. If you look like a girl, but sound and walk like a man, chances are that you’ll be seen as a crossdresser instantly. With that in mind, take some time to train before you go for the first time to a women’s clothing store. Here is an article can help you.

Last, but not least, you’ll have to consider how long you can crossdress outside comfortably. So, if you happen to get tired easily, it’s better to choose a store near your house and spend less time browsing for stuff. Your resistance may vary for different climates, weathers and outfits, so consider that.

The advantages of this method are in the fact that a crossdresser will draw less attention than a man buying women’s clothes. The main disadvantage is the lack of reliance, since it works differently for each person and context.

3. Coming up with an excuse

This method is also common and effective, specially for purchasing a small number of items, and I’ve used it a couple of times. The objective is to come up with an excuse that justifies what you are buying. You can simply say that it’s for someone else, or lie about your intentions, but you can also get creative and come up with something more complex. Saying that it’s a gift tends to work better, but you can also make use of the context. To avoid suspicions, say it’s a mother’s day gift, or a valentine’s day present for your girlfriend. If you are buying lingerie, bras, and underwear, say that you want to spice up your relationship. It tends to make people uncomfortable and they stop to ask you questions

The context can be used to a larger extent, actually. The current season, for example, is a wonderful opportunity. You can go to stores specializing in women’s clothes, and buy a few things under the pretext of making a Halloween costume for a friend. Wigs also tend to be on sale during this time of the year, and in certain regions, it’s pretty common to dress up as a girl for Halloween. With that in mind, take a calendar, and plan your first visit to a store that sells women’s clothes near date or holiday that you can use as an excuse.

Make sure to check the gift return policy on the stores you visit. If they allow returns and exchanges, you can buy stuff without being afraid that it won’t fit. Buy what you want under the correct pretext, and try it at home. If the item doesn’t fit, you may return it to the store!

Here, the advantages are that any crossdresser can do it, and being able to try the outfits at home. However, it has a downside: It won’t be as effective if you want to buy a lot of things or make regular purchases at the same store.

4. A few more tips on confidence

Well, practice is an important thing not only for your crossdressing skills. Practicing your conversation skills and your technique of choice is going to improve your confidence. A way to do that is to go to masculine clothes stores, and pay attention to common phrases and interactions that happen there, and take note of what you hear.

Once you get back home, get a mirror, and put it right in front of you. Start to say these phrases out loud, while you look into the eyes of your reflection. It helps you to lose your fear and prepares you for real face-to-face interactions.

Your confidence will improve, and you’ll have an idea of what to say if someone asks you anything at the store. Such exercises are very important, especially for first timers that don’t know what to expect. They are also helpful for those that choose to crossdress at the store, since it’s also a good way to train your female voice.

Going out to shop at a store that sells women’s clothing is a huge step for lots of crossdressers. Once you overcome your fear, you’ll be able to better experience that. Until then, you can make use of these tips to prepare yourself. First-timers may have some difficulty building confidence. But they can take their time and practice until they feel that’s enough.

Many methods are available, and that shows how important it is to be prepared before stepping inside a store. Read my tips carefully, and be realistic about your current situation. Once you understand them, you’ll be able to decide which one is ideal for your case.

What did you do when you first went shopping in a women’s clothing store? Did you use any particular skills or experience? Come on, share it with everyone in the comment section.