Choosing Your Cross-Dressing Underwear for Different Occasions

Feminine clothing differs from its masculine counterparts in many different aspects. We must learn those differences and adapt our outfits for different situations. It includes even the simplest things, such as underwear. But how should you choose it? If you pick the wrong kind, you might suffer from discomfort or something even worse.

If you cross-dress for multiple purposes, such as to stay home, hang out with friends or even go to work, you should choose your underwear accordingly. My goal here is to provide you with some other examples of that and help you choose the best underwear for each situation. So if you want to feel as feminine and comfortable as possible, read my tips in this article!

1. Staying home

Most cross-dressers dress up at home, especially those still beginning their journeys and haven’t come out yet. Many of our sisters will relate to this situation, so I guess it’s worth making it my first topic here. Well, what do I mean by it? I’m talking about those ordinary sessions we do at home, sometimes in a hurry, that tend to be short. You should think about what you consider to be important in this scenario.

For most of us, the goal is to look pretty and feminine for no one but ourselves. Hence, I recommend you choose something you think looks great on you. A suggestion would be decorated polyester panties, which are pretty feminine and comfortable. They come in many different colors as well, which makes them suitable for a wide range of styles. I’d go with black or dark red for generalization purposes, but pink is another good choice. As for the decorations, the most common are tiny pearls or ribbons. They might require a bit of tucking to conceal the volume down there, but most of us don’t mind it when we are home alone.

2. Longer sessions

For longer sessions, such as when we plan to spend the day en femme, it’s essential to wear something comfortable. With that in mind, I wouldn’t recommend tucking for this scenario. Rather than that, use panties made of elastic cotton or other malleable materials. Unless you plan to spend most of your day in underwear, there’s no point in choosing your panties based on how they look. Instead, your priority should be how comfortable they feel. Stretchable cotton is the ideal material, as it’s rather cheap and will easily accommodate your “manhood.”

Another thing to consider is color. If you plan to stay as a girl for that o long, you may sweat down there, and it might stain your panties. Said stains are difficult to remove from dark fabric, so I recommend you choose nude tones for this purpose. You should apply this logic to any scenario in which you plan to dress up for more than a couple of hours, as long as you don’t want to show your underwear. I’ll elaborate on that through the next couple of topics.

3. Going out with friends

Suppose you plan to go out with your friends while en femme, keep in mind a few things. Consider, for example, the amount of time you’ll spend and how you’ll go from one place to another. Climate and weather may also play a role in your choice, but it’s not as significant. I am also supposing that you don’t plan on showing your underwear to anyone else. If that’s the case, you may find useful tips on the next topic, where I talk about the best underwear for a date. Meanwhile, let us think about a normal scenario of a casual night out with some friends.

If you go by car, you won’t have much to worry about. Remember, this time you won’t be alone, so tucking is a great idea, as it makes you more likely to pass as a woman. A good option would be to wear a gaff, as it allows you to tuck more comfortably. If you end up Using tape, avoid the strong ones, as they might hurt you. Try medical tapes instead, as they can hold things in place even though they’re easy to remove. Besides that, you might feel free to choose anything that makes you feel feminine. But I still want to recommend something practical. Another advantage of gaff panties, for example, is that they are easy to remove and wear again if you need to use the bathroom.

If you plan to walk, things may be a little different. Wearing feminine underwear and tucking can make walking something quite uncomfortable. Because of that, when I have to walk en femme, I don’t tuck. I use comfortable panties or even my masculine boxers underneath my cross-dressing outfit. That’s just so I can walk without getting too tired before getting to my destination. But I do carry some of my gaff panties in my purse, so I can go to the bathroom and change into them as soon as I arrive. This is a versatile strategy, as It allows you to prioritize feeling feminine or comfortable when you want to.

4. Preparing yourself for a date

This is the interesting part, as it finally involves someone else potentially seeing you in your underwear. I’m also using “date” here as a generic word since this section applies to any relationship. But the general idea is that there will be some degree of intimacy, at least enough to make this kind of scenario possible. In other words, I’ll be giving tips regarding which kind of underwear cross-dressers should wear in the presence of their partners.

Let’s start with the basic stuff. When it comes to intimacy, lingerie comes to mind. They have lace patterns and come in various different shapes and sizes. Some of our sisters like to add hosiery with garters and other fancy stuff, but it’s optional. The taste for underwear varies between relationships, but good yet simple lingerie works in most cases. With that in mind, I say that cross-dressers should avoid thongs or thin panties. These are just uncomfortable and don’t help that much in feminizing yourself. Try normal-sized or gaff panties instead. And if possible, experiment with those larger, more comfortable lingeries.

Depending on your goals in terms of intimacy, you could make use of silicone panties with faux genitals. They help you to get the most feminine experience possible in bed if that’s what you want. Some models even have in-built tucking mechanisms for your friend down there, which can be more than useful. The ideal is to combine it with panties of your choice, preferably lingerie for this occasion.

5. Dressing up for work

One good thing about dress codes at work is that they never say a thing about your underwear. Because of that, our sisters may have the opportunity to extend their cross-dressing experience to their work hours in a subtle way. The idea is to wear panties instead of boxers for the feeling of it. No one else will notice, but you’ll still get some of that feeling of cross-dressing in public. It did give me chills the first time I went to college like that.

But to make sure you can get the most of it, you must choose wisely. Keep comfort in mind as always, and avoid tucking. You don’t want your coworkers to notice that something is missing down there. Besides that, make sure you’re wearing some that you can remove and put back with ease if you ever happen to go to the bathroom. Nude tones are better for long periods of usage since they’re harder to stain. But then again, color here is irrelevant unless you have a very specific set of preferences. As for the fabric, cotton or polyester might be the best two options.

6. How to sleep comfortably in female underwear

Last but not least, how can a cross-dresser sleep while wearing panties? This is where we prioritize comfort as much as possible. You don’t want to wake up because of that. What you want is to have a pleasant experience and a good night of sleep. Luckily, I do have a few tips for that as well.

My rule of thumb for choosing something to wear when I’m going to sleep is to make sure it’s loose instead of tight. A perfect fit is more on the “tight” side of things, so I tend to avoid it. The size selection is to make sure your panties won’t enter areas where they shouldn’t be overnight. But the most important thing to get right is the material. Polyester panties, for example, are not so malleable and thus, may feel uncomfortable. What you want is a material that is both malleable and lets your skin breathe through, such as cotton or microfiber.

With so many different kinds of underwear and scenarios, some cross-dressing may end up confused. There are way too many options and combinations, so it’s normal to be overwhelmed. But in the end, we must analyze the situation and define a few priorities. Be it the looks, the comfort, or even the practical sense of it. It’s possible to find the perfect pair of panties based on this information, so good luck in your journey! We would really love to hear what you have to share about it. If you have any experience with feminine underwear, leave a comment with your recommendations!

Quiz:

Which of these materials do you think is the most versatile for panties?

A. Cotton

B. Polyester


C. Microfiber

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