Davina - Lets see how this article pans out again commenting as reading it for the first time.

Crossdressing is a fun activity that almost everyone one way or the other engages in. 

On weekends or during holidays, when most people relax at home or go out with friends, crossdressers tend to dress up in female clothing and go out for fun activities such as shopping for clothes, attending parties, or even going on dates with other crossdressers or transgender people. 

If you’re a crossdresser, then you know that there’s nothing quite like the thrill and feeling of dressing up in women’s clothing.

The way in which it hugs your curves and makes you feel sexy is just phenomenal. 

Crossdressing can be a lot of fun, but it can also be a bit daunting if you’re not sure where to start or some fun stuff to do. 

As a crossdresser, you will find this article very helpful. 

Davina - Lets hope so 

You can do many things as a woman that most men cannot. 

You can go out and buy clothes just like any other woman, without worrying about the price or whether they fit correctly. 

Davina - Oh I worry about the price and if they fit currently. I’ve never shopped as Davina unless I count the one time i went to Tesco dressed when away with work and typically in the fem clothing section didn’t see anything worth buying.

You can also experiment with makeup and jewelry. 

This list of activities is just one way of exploring your feminine side while having fun!

Experiment with makeup 

Crossdressers love experimenting with different kinds of makeup. 

There are so many colors and techniques to try, making it such a fun activity for crossdressers. 

You do not have to step out of the house if you do not want to; experiment in front of your mirror at home or while using the camera on your phone. 

If you already know how to apply basic foundation and other types of cosmetics, this should be easy for you since there is no right way to put on makeup anyway.

Davina - I need to experiment more as I’ve sussed one look and its my go to every time.

Remember that any mistakes made when applying makeup will help increase your skill level next time. 

It’s all about practice, after all. 

Even professionals practicing their trade may end up looking bad. 

The only difference is that they have to go out in public with whatever mistakes are made. 

You can stay indoors, and no one will see but yourself.

Wear a wig

 Davina - For any crossdresser who hasn’t got a wig, for me I was dressing without one and sometimes applying makeup but the first time I saw myself with makeup dressed, put on the wig then looked in the mirror wow there was Davina for the first time .. The piece de resistance the wig completes the look and to this day I always finish my transformation by putting on the wig et voila theres Davina.

Why not try wearing one of those long wigs that women wear if you have short hair? 

There are so many different styles available. 

You can even buy synthetic ones that do not cost much and look natural when applied correctly. 

They will add to your femininity in no time. 

Just be sure to keep these items away from direct heat sources such as fireplaces or space heaters since they may catch fire. 

However, it is best to quickly place the item into a bucket filled with cold water before allowing it to air dry naturally.

Of course, some men already have long hair or wear wigs regularly as part of their everyday life. 

Wear a dress 

One of the most popular activities for crossdressers is wearing dresses. This can be done in so many different ways, and there are no rules when it comes to what type of dress you choose to wear. 

You could go out and buy a brand new one or borrow something from your female friends or family members.

Davina - Tip if your wife is a size 12 and you’re a size 16 you aint gonna fit in her dress so please don’t try and rip one of her dresses. That would take some explaining. With Temu, Shien and other on line shopping you can get some very reasonable dresses. 

If you have never worn a dress, start with something simple like a sundress or knee-length skirt and blouse set. 

Remember that comfort should always be your top priority when choosing an outfit, whether you are crossdressing or not. 

If the outfit is uncomfortable, you will not enjoy wearing it – regardless of its appearance. 

It is also essential to choose an age-appropriate outfit. 

You do not want to wear something too flashy or revealing if you are going out in public. 

Wear high heels

Davina - I love hight heels on women and love how they shape my legs I’m not a t girl who wears flats.. If I’m dressed its 3 inch heels minimum for me.

High heels are not just for women; crossdressers can also wear them. Many men look even more feminine when wearing high heel shoes. 

This is a great way to add height and curves to your body if you need them. 

Just be sure you are comfortable walking in high heels before wearing them outside the house. 

Knowing this is intended for you to have fun is important. 

Nothing is worse than taking a few steps and then having to stop because you are in so much pain. 

You may also want to try a pair of heeled sandals or pumps rather than choosing a stiletto heel since these are a little bit easier to walk in.

Wear a skirt

Another popular item of clothing for crossdressers is a skirt. 

This can be worn with a blouse, t-shirt, or dress. 

There are different styles and colours to choose from, so you will surely find one that suits your personality and style.

Just like with dresses, it is vital to choose an age-appropriate skirt that is comfortable to wear. 

You do not want something too tight or loose; it should fit well but not too constricted. 

If you are wearing a longer skirt, then be sure to pair it with flats or low heels instead of high heels since these will make walking much more difficult. 

Go out in public 

Many men who crossdress are afraid to go out into the world as a woman, but there is no reason for this fear. 

There are places where you can feel comfortable dressing up and going, whether with friends or by yourself. 

You do not have to dress entirely from head to toe if you don’t want to since most people will never notice your outfit unless they make an effort.

Davina - i would say the best tip is dress to blend in not stand out and tone down the makeup to look more natural and a convincing wig with a good style. 

You can also choose a time when fewer people will be around, such as early morning before work starts for the day, during lunch break, or after everyone has gone home for the night – whatever works best for you at that particular moment in time.

Davina - Also have an exit strategy if things do go wrong how you’re gonna get out of a situation of being read or ridiculed.

 Enjoy a night on the town

A great way to spend one’s evening is by going out with friends who crossdress. 

Davina - I’ve mentioned before I’d love to go out with my wife and her friends as Davina (Never gonna happen) and this is on my bucket list to maybe go out with some t-girl friends and i’ve heard of a few events but miles away needing it to be a weekend away and cost. One day..

Sometimes it can be difficult to spend time alone as a woman, and you may still feel like you are hiding something from everyone. 

Going out in public crossdressed can help alleviate these feelings of isolation or loneliness. 

Davina - I’ve been out for a walk, to get something from the car and to Tesco when away with work and once in London with my wife. Each time it was exciting only nerve wracking the very first time I left the hotel when away with work, every other time was fine.

There will always be others who understand what it feels like to wear women’s clothing – even if they do not necessarily share your taste in fashion.

You could go for dinner at a nice restaurant where people dress nicely and order drinks before heading off to another location, such as a bar or nightclub. 

You can have as much fun as possible and leave whenever you want, making this activity one of the more carefree options. 

Go girly shopping 

Crossdressers are always looking for new ways to have fun and get creative, and what better way to have fun than going shopping? 

Davina - I’ve been Davina shopping with my wife but never as Davina but typically when I’ve gone with intent to look for a new skirt, blouse, dress, heels, boots etc I’ve seen things when with the family and thought oo id like that then gone back just me and Esme a few weeks later and its gone and I’ve had a trip specifically looking for something for Davina and come home with a top up of makeup but no new clothes. On line is probably you best bet but another on my bucket list to shop as Davina (other than that one trip to Tesco)

Traditional men mostly wonder why women always seem to have so much fun when shopping.

Davina - I actually like shopping if it’s done to a purpose and it’s not all day lol

As a crossdresser, you can just as much experience such joy and freedom that comes with this activity. 

Furthermore, you can significantly improve your feminine mannerism and connect deeply with your feminine side. 

You can go shopping just by yourself or with your girlfriends and do stuff like bargaining on prices, getting the best deals, checking up on the latest fashion styles, and more.

Shopping is a kind of ritual for women, a sort of can’t do without, a save space for bonding and doing girly things. 

That’s why as an MTF crossdresser who wants to have some really good fun time, shopping is arguably your best option. 

Attend a crossdresser event

Davina - Something I’m yet to do but on my bucket list.. I don’t think Esme would like me attending an event with other crossdressers but a nice social event with everyone dressing at a club or pub whats the harm..she may enjoy it if she came along too. 

Many events cater specifically to those who enjoy dressing up as women, which can be a lot of fun. 

It is indeed a great opportunity to meet new people, learn about different products and services, or chat with other attendees in a more relaxed setting. 

If you do not live near any large metropolitan areas, consider checking online for upcoming events in your region.

 There is sure to be something available, regardless of where you reside.

 Go to the movies

When you go out dressed up, do not forget that it is also possible to enjoy some time alone by seeing a movie in theaters. 

It can be fun trying your best to blend in with other people in public while wearing women’s clothing; this will make for an exciting experience when sitting next to others who probably wonder why you look so out of place.

 Davina - We need to look to blend in not look out of place and i would suggest if you do go to a movie if someone talks to you keep the reply short and try to sound as fem as you can. I remember in a supermarket myself and Esme heard an “Excuse me” in a deep voice, we moved the the side as a T girl walked past us.. Also sporting a 12 o clock shadow.. So tip blend in to pass and maybe work on your vocals as a tgirl.

It may even help if you bring along someone, like another crossdresser or your girlfriend, who would understand what it feels like being surrounded by strangers while dressed up. 

They could act as your bodyguard and swoop down on anyone who tries giving their opinion about how ridiculous you look – remember that violence should only ever be used as a last resort.

Have a spa day

Davina - Meh.. Esmes mentioned a Spa day to me but it doesn’t appeal and i dont think i’d do one as Davina.. Maybe do a makeovr day but a sap day not my cup of tea

One of the more relaxing activities you can enjoy as a crossdresser is having a spa day. 

This could involve either going to an actual spa or simply pampering yourself at home with some beauty products and treatments. 

There are many different types of spas to choose from, so take the time to research and find one that offers services that appeal to you. 

If you have never been for a massage before, then this would be the perfect opportunity to try it out; make sure that the masseuse does not mind if you happen to get a little bit too excited during the treatment. 

Wear lingerie under your clothes 

Davina - I’ve done this a few times in the past and tried it recently to see if it helped lack of dressing and it doesnt (for me) .. I’m an all or nothing tgirl i need the makeup the full look or I don’t dress which is kinda limiting but dont write this off it may work for you.

For all those crossdressers who want to wear something sexy underneath their regular clothes; it does not matter if you are at work, school, or even in public. 

Both men and women can wear lingerie, but the difference with these items, compared to what typical females might buy, is that they tend to be a little more risqué. 

Many lingerie pieces available online feature crotchless panties, allowing you complete access at any time. This could come in handy when taking care of certain urges during your day without worrying about finding somewhere private enough not to leave behind evidence.

Davina - What the hell does that mean?

Go out shopping dressed 

This is the most common activity among crossdressers that go out dressed up. 

It’s also practical, and can serve as a form of practicing. 

It depends on your confidence, but shopping as a crossdresser may create a lot of new possibilities for you. 

For example, you can go to the women’s section and buy stuff there without drawing too much attention. 

Besides that, you may be allowed to try out the outfits before you buy them, making sure your new feminine garments fit you.

Davina - Bucket list but how open are shops to letting t girls try things on? Anyone?

 If you’re trans, it’s common to experience gender euphoria while doing that, adding an extra advantage to the activity. 

You don’t even have to buy anything, actually. 

You can use it as an opportunity to do a quick price research and to crossdress outside. 

And if you pay attention to trends, you can plan your seasonal outfits based on what people are buying. 

Go to a crossdressing club 

Crossdressing clubs are places in which you can learn a lot, and meet new people. 

It’s an awesome experience, which every crossdresser should have. 

You’ll feel as part of something else, and notice that many people are like you. 

This kind of knowledge helps to improve one’s self esteem, and encourages you to keep crossdressing. 

Besides that, in a club you can learn and practice new crossdressing skills in real time. 

You’ll have access to many tools and materials, as well as assistance from more experienced crossdressers. 

With that in mind, most crossdressers can benefit from clubs, especially the newcomers and novices.

Davina - One day maybe, I suppose less threat / pressure than being out in public as a t girl. 

Cosplay your favorite female character

Davina - Harley Quinn is the one I’d go for.. 

Cosplaying is a fun activity for both crossdressers and non-crossdressers. A cosplayer is someone that dresses up as their favorite character from a movie, show, video game, etc. 

They generally show up at events and conventions, such as comic con or game conventions. 

If you are a crossdresser, the characters you cosplay aren’t limited by your gender. 

This subcategory of cosplaying while crossdressing, is known as crossplaying. 

You can even use that as an excuse to dress up as a girl without outing yourself, as I did a few years ago.

 Do a photoshoot

Photoshootings are also a must do for crossdressers. 

It’s not rare either, and you can learn some photo techniques with other crossdressers as well. 

Some clubs may also feature photo shooting areas to encourage the practice. 

I like to recommend it for crossdressers because it has many advantages as well. 

The results tend to be something more professional than a selfie or mirror pic, and allows you to see how you actually look. 

You can use these photos to pinpoint what works for you, and what does not, so you can improve your skills. 

Or maybe use them as a means of remembering you from your crossdressing self, which is useful to deal with body dimorphism.

Davina - I would like a makeover and a photo shoot to see how feminine a proper makeup artist / stylist could make me look but its so expensive. 

A girls’ night with other crossdressers 

This is the best way to interact with other crossdressers and make new friends. 

Davina - Esmes said she’d not like it if i started going out as Davina but it is something i see on flikr tgirls out together having a laugh and maybe something I’d like to try .. i’d want her to tag along too as i think she’d enjoy it.. Especially with some of the fab t girls from this forum and their wives.

The place doesn’t actually matter though. 

You can go to a restaurant, a pub, a bar, a movie theater or even to a walk. 

What is really important is the company. 

The real experience comes from spending time with other crossdressers. 

It helps you to develop more confidence and lose the fear of going out. Their company gives you courage to do things that might have been hard to do alone. 

That’s something every crossdresser should try out at least once, just to feel the warmth of being in a crossdressing group. 

Besides that, friends that you make this way tend to stay in touch. 

If you are insecure, talk to your crossdressing friends about it, and ask for their support. You won’t regret it. 

Be engaged with the rest of the crossdressing community 

Davina - you’re here reading the forum so you are engaged with a number of t girls already.

You can feel the aforementioned warmth even if you don’t have any crossdressing friends. 

Thanks to the internet, it’s easy to stay in touch with the rest of the crossdressing community, through forums and blogs such as this one. You can interact with crossdressers from all over the world, which allows you to have contact with many different views. 

By interacting with them, you’ll be exchanging knowledge, and helping the community itself to grow.

Davina - to an extent adding articles here and interacting with the forum members and chatting on tv chix makes up in a small part for times when I can’t crossdress.. When i chat I chat as Davina mostly about any old subject. It’s just nice to chat with others like us. 

Experimentation 

There’s no better way to learn who you are than by experimentation. 

If you are in doubt about what kind of crossdresser you are, and what your gender identity is, you can find answers this way. 

I recommend you try out as many ideas as you have about crossdressing. 

Mix up some outfits, try out discovery styles until you find out what suits your personality. 

About your identity, try to see yourself living as a woman, and try to notice if you feel like something else. 

It’s a discovery that is aided by experimentation and empiricism. 

This activity helps people to understand who they are on the inside, and to be themselves. 

Due to that, I highly recommend that every crossdresser should try it at least once. 

Try secret crossdressing 

This tip is quite helpful for crossdressers that are unsure of who they are, or who are unable to come out. 

But crossdressers with little time, or that want to extend their experience, can also benefit from it. 

A good example of this activity is to wear feminine lingerie under your masculine outfits. 

Go to work using panties or use a sports bra to school, no one will notice. It’s subtle, but you’ll feel the difference. 

Of course, it doesn’t make you pass as a woman by itself. 

But it can be done as an exercise to improve your confidence and amplify your crossdressing experience. 

Another subtle touch, but a bit more likely to be noticed, is wearing feminine perfumes and a little makeup. 

The trick is to make sure you’re comfortable, without crossing your boundaries.

 Keep a crossdressing diary

 Davina - Or a Blog!

A diary is very useful to keep track of your progress as a crossdresser. Take note of every session, and detail what you did during each one. 

Davina - Be careful if youre in the closet of leaving the diary about for someone to pick up and read and the same with a blog if you want others to read with you the Anon that’s ok but leaving it open on your laptop or phone / tablet for someone to see then you’ll have some questions to answer ie why are you reading a crossdressing blog.. Omg youre writing a crossdressing blog? Are you a crossdresser?? If you share a drive or laptop I’d suggest erasing the search and internet history if you dont want to be traced / found out by someone at home.

If you’re writing an online journal, you can attach pictures of each session, so that you have visual feedback. 

Tracking the skills you learn allows you to understand how each one of them affects the final result, and how efficient they are. 

Once you look upon your progress, and realize how far you’ve come, you may feel proud and notice an improvement of your self-esteem as well. 

Davina - My initial blog helped me get my thoughts down and i got feedback from others and i then shared it with Esme who wrote a few blog posts in there herself but i think i used it also as a way of communicating with her putting my thoughts and feelings into the blog with her reading it it gave her a picture of what was going on in my head and a better perspective why i crossdress and it turned out it helped others also.. And now we have the forum which replaced the blog.

If you’ve been crossdressing for a while, make the comparison between recent pictures and others from a few years ago! 

It also works for transgender people doing hormone therapy. 

Enjoy your free time

Embrace crossdressing once and for all. 

You must learn that crossdressing doesn’t require any special occasion, nor any specific activity. 

A good way to practice this notion is to dress up to spend your free time at home. 

Davina - I would say if you have opportunity and need to crossdress take it - I’m guilty of putting it off and i don’t have that luxury any more with opportunities rare.. So have an opportunity take it.

Dress up as a woman, and stay comfortable doing whatever you want!  It helps you to release your inner girl, and feel more legitimate as either a crossdresser or transgender person. 

What I mean is that it allows you to stay in touch with your gender identity and inner self on a daily basis. 

It helps to normalize other aspects of yourself, and to get familiarized with these expressions. 

Crossdressing is a broad term, with many different aspects. 

Each crossdresser is unique, with their own necessities and demands. But we do have a lot of things in common as well. 

I’ve selected these activities based on common struggles and desires among crossdressers. 

That’s why I consider them to be things every crossdresser should do, at least once just to try out. 

But be patient, and there’s no problem if you want to keep your boundaries. 

Feel free to experiment and see what works best for you. 

Have you tried some of these activities before? 

Let us know by describing your experience in the comments!