Some Fun Activities for Crossdressers


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.


Some Fun Activities for Crossdresser


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. 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. You can also experiment with makeup and jewelry. This list of 12 activities is just one way of exploring your feminine side while having fun!



1) 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.


Some Fun Activities for Crossdresser


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.


2) Wear a wig


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.


Some Fun Activities for Crossdresser


Of course, some men already have long hair or wear wigs and contacts regularly as part of their everyday life. Some may even wear skirts instead of pants at home on weekends because they find this activity fun and exciting. If so, be sure to keep those items away from small children who might mistake your outfit for something else entirely and pull on it with all the strength that only a child can possess.


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


Some Fun Activities for Crossdresser


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.


4) Wear high heels


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.


Some Fun Activities for Crossdresser


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.


5) 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 colors 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.


6) 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.



Some Fun Activities for Crossdresser


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.


7) Enjoy a night on the town


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


Some Fun Activities for Crossdresser


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.


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


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.


Some Fun Activities for Crossdresser


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.


9) Attend a crossdresser event


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.


Some Fun Activities for Crossdresser


Some popular events include the yearly Miss Gay America pageant, which takes place across the United States, transgender beauty pageants such as Transworldasia in Singapore, and even balls where participants dress up in their most delicate gowns and tuxedos. 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.


Some Fun Activities for Crossdresser


10) 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.


Some Fun Activities for Crossdresser


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.


11) Have a spa day


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.


Some Fun Activities for Crossdresser


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.


12) Wear lingerie under your clothes


The last activity on our list is 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.


Some Fun Activities for Crossdresser


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.


Some Fun Activities for Crossdresser


There is no limit to the level of fun you can have while crossdressing; whether it’s going shopping or doing a photoshoot, bike riding, massage, cosplay, makeup, etc., you can be sure of having the best time. These activities can reduce stress levels and take your crossdressing to another level. Crossdressing in itself is fun. You can get to live out your feminine dreams while maintaining your lifestyle. Just remember to be yourself, be confident and daring, and above all, have fun!

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  1. Thak You, SO much I need more confidence. I am so happy i read your tips. I will keep these in mind. And knowing many others like me are out there just need to find out where I can meet them. Any tips?

    1. You’re welcome! Sure, we have many articles on our blog that talk about this. I suggest you start by meeting some sisters from the internet(This article will help you, and if there are crossdresser makeup studios or drag queen bars in your city, you can go hang out there and you will meet a lot of friends there too. Trust me, you’re never alone in your crossdressing journey!

  2. I am 52 year-old closeted crossdresser who wants come out to my girlfriend of two years I am very afraid also excited that I could be free to enjoy activities such as these I’m tired of hiding I want friends like me

  3. I would ask the question, “How do you feel with guys wearing a dress?” If she’s fine with it, I would coming out as a crossdresser to her. Even, then I wouldn’t go out in public as a crossdresser. The only I’d wear is nail polish and nothing else that’s feminine in public. That’s because I don’t want guys thinking that they can have sex with me. I’m a straight guy which means that I like girls. I wear a dress, because it’s comfortable for me to wear.

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