What Can We Do to Maximize the Fun of Cross-Dressing?

Cross-dressing is supposed to be a light-hearted, fun activity.

A cross-dresser’s goal is to have fun and enjoy their time in as many ways as possible.

However, if we limit ourselves to the basic stuff, we might be missing some amazing opportunities.

We can do so much more than dressing up at home.

There’s a whole new range of experiences out there for you to try!

Focus on buying stuff that you like, and use your free time to discover new cross-dressing techniques.

You can also maximize your fun by sharing your experience with more people or going out en femme.

Here, I’ll talk about the many ways you can maximize your cross-dressing fun.

So if you want your experience to be more fulfilling, don’t miss out on this article!

1. Buy clothes that make you happy

Shopping for new clothes is always a good way of revigorating your cross-dressing excitement.

Adding new stuff to your wardrobe means that you have new combination options to try out.

It incites you to cross-dress, so you can see how you look in each of them.

But shopping with no criteria is useless. You must learn to choose outfits and plan your purchases according to your preferences.

For example, instead of buying random stuff at stores just so you can try them out, save some money and buy a particular outfit.

We all have our unique styles and preferred clothes, so make sure you list yours.

It will help you to have more fun, creating a special moment for cross-dressing.

Trying out these outfits for the first time is always a  thrilling experience.

The best part of it is that companies are selling clothes that fit most sizes.

You may even shop online to preserve your privacy, which grants you access to a wider catalog as well.

This way, we are more likely to find something that fits our style and makes us happy, improving our cross-dressing experience.

Start by choosing clothes you have always wanted to try.

Before we start to cross-dress, it’s common to think about ourselves as girls with specific outfits.

It’s influenced by our preferred styles or by other girls we see at work or school.

Make a list of everything you wanted to try back then, take some measurements, and browse the internet or thrift stores for these items.

If you have more confidence, you may even go out shopping and try out a variety of new outfits before buying!

All of that will contribute to the experience.

2. Invest some time into learning new stuff

Innovation is always good when it comes to cross-dressing.

I mean, you can keep doing the same stuff you’re used to.

However, you’re less likely to improve your experience if that’s the case.

We tend to become so good at it that we no longer feel that sense of accomplishment if you know what I mean.

There’s a complex scientific explanation to that, which has something to do with serotonin, but that’s not my point.

What I’m telling you is that we tend to fall into a monotonous routine If we base our cross-dressing on a limited set of skills.

Seek more knowledge, watch tutorials, and read stories of other cross-dressers.

This way, you’ll learn new stuff that might be useful.

Doing so will bring a certain degree of variance to your routine, widening the range of possibilities.

Once you learn new stuff, you’ll want to try it yourself, having fun in the process.

And all those feelings of accomplishment will be back once again.

Take a look at your schedule, and see how much free time you have.

As a rule of thumb, try to use about a third of that time for cross-dressing stuff in general.

And about half of the said third can be spent in learning new stuff, at least twice a week.

Follow cross-dressers on YouTube and social media to keep yourself updated with new techniques.

And visit forums and blogs such as this one. It allows you to learn from other people’s experiences!

And don’t worry about your search history, even if you’re a closeted cross-dresser.

You can open an incognito mode tab (Ctrl+Shift+N on Google Chrome) and create a new e-mail for that.

3. Put more effort into the makeover

When we first start to cross-dress, we put all of our efforts into creating the perfect makeup to feminize our face.

We choose clothes carefully to complete the look and wear a lot of shapewear.

But it’s common to become somewhat sloppy with time.

We put less effort into our makeover because we have already got that first impression, and cross-dressing becomes a chore after that.

We pay less attention to detail and wear whatever looks comfortable.

There’s nothing wrong with that, much the opposite, as normalizing cross-dressing is good.

But whenever you feel like you want to have more fun, put more effort into your transformation.

The chances are that you’ll be surprised with how good you look dressed as a girl.

If you want to make sure you’re putting as much effort as possible into it, I have some useful tips.

Once again, checklists can come in handy.

Make up a list with all the cross-dressing techniques you know, and apply them in order.

But pay attention to each one of them! If you have someone else to help you, that’s even better.

They can give you real-time feedback, or you can send some pictures and ask about how you look.

It gives you a new point of view, with new parameters to measure the effort.

4. Try new gadgets

Another thing that shows how innovation improves cross-dressing is the use of gadgets.

There are a whole lot of products out there designed to help cross-dressers and trans people look more passable.

Others are there to make your experience more comfortable and practical.

Gaffs and breast forms, for example, are interesting gadgets that not every cross-dresser use.

But those that do use them look way more convincing and passable as women.

Products like masculine or trans-friendly panties and shapewear, on the other hand, aim at reducing pain and discomfort.

They make us more comfortable while en-femme, so the experience becomes far more enjoyable.

And feeling like that allows us to have more fun as cross-dressers.

To choose the perfect gadget,  think of what you feel like you’re lacking.

If you want a better cleavage, try breast forms or push-up bras.

Gaff panties will make tucking comfortable, while silicone bodysuits will hide shapewear.

This way, you can wear more revealing stuff.

It all comes to your personal objectives as a cross-dresser since there are gadgets to solve most of our problems.

They help us overcome challenges, and the result is, of course, a more pleasant and fun experience.

5. Go out every once in a while

Being a girl outside is a completely different experience from doing so indoors.

If you’re a person who loves adrenaline, this is granted to improve your experience.

We never know how people will react to seeing us, as we can’t be sure about how passable we are.

But the feeling of going out as who you are on the inside is priceless.

Besides that, the chances are that you’re more passable than you think, and people may be more receptive as well.

Being referred to in feminine pronouns and perceived as a girl is awesome and a dream to come true for most cross-dressers.

Because of that, this activity is one of the most rewarding ones in terms of fun.

You can start by going for a walk in a calm neighborhood, so you can get some fresh air as a girl.

But the most common form of interaction with the outside world as a cross-dresser is to go shopping en-femme.

Most of our sisters use it as an opportunity to enter stores that sell items for ladies, ones that they wouldn’t dare enter in boy mode.

It also helps them with confidence to try out some outfits at these stores to see how they look in them.

The dialogue is often minimal, so voice training is optional.

But if you want to put your female voice impression to the test, eat outside.

Ordering food is a good way of getting better feedback about how feminine your voice sounds.

6. Share your experience

You don’t have to cross-dress alone either. Doing so can get boring quickly if you’re more of an extrovert.

Because of that, I recommend you find someone to share your experience with.

You are more likely to find a comprehensive significant other in your teens.

But if cross-dressing in a relationship isn’t for you, try meeting other cross-dressing friends.

Go to a drag queen club and LGBT bars while en femme.

You’ll meet a lot of cool people who can cheer you up and even give you some advice.

Being near these people shows that you’re not alone.

Besides that, going out with these people allows you to take part in a number of group activities, such as parties and hangouts.

You’ll make friends and spend time with them while cross-dressing.

What can be more fun than that?

You can find this kind of people in cross-dressing groups on social media or even on dating apps.

Our community grows stronger every day, and I’m sure you’ll find someone near you to hang out with.

If you become close friends, you can even cross-dress together, learning from one another and giving real-time feedback.

This kind of collaboration will improve the cross-dressing experience for both of you.

And as the saying goes, the more, the merrier.

The universe of cross-dressing is broad and very rich. There are many different ways of enjoying and experiencing it.

But even though it’s more of a personal thing, some general tips can make everything more enjoyable.

These are some of those things that worked for me and vastly improved my cross-dressing experience.

They helped me keep myself motivated and never give up.

I hope you find those tips exciting and that they are as helpful to you as they were to me.

And if you think they’ll be, leave a comment!

Quiz:

Which tips do you think will be the most enjoyable?

A. Buying new stuff that you like


B. Learning new stuff


C. Sharing the experience

Get Results

Written by Elise