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Best 10 Crossdressing Dares to Try

05/11/2023 BY Marie

As a crossdresser, you should not restrict yourself to just dressing up, putting on makeup for some time, and then returning back to normal life. Dressing up and putting on makeup is exciting in the initial days but after a point of time, it gets boring and unsatisfying.


Best 10 Crossdressing Dares to Try


To truly enjoy the experience of crossdressing, it’s important to not only wear feminine clothing but also adopt feminine behaviors and incorporate them into your daily life.


In this blog, I will give 10 crossdressing dares that you should try to have a full feminization experience and reignite the excitement of crossdressing.

10 Crossdresser Dares


Do Full MTF Transformation


Best 10 Crossdressing Dares to Try


Let’s start with an easy crossdressing dare that involves a full male-to-female transformation, including a wig, makeup, and a sexy dress. If you haven’t tried this before, trust me – you’re going to fall in love with your feminine side! To begin your transformation, start by taking a relaxing shower to ease your nerves.


Best 10 Crossdressing Dares to Try


Since this is a full-body transformation, everything on your body should be feminine, starting with your undergarments. Choose a favorite bra and panty that fit well and complement your outfit. When it comes to crossdressing, don’t skip lingerie – it can make all the difference in your experience. Next, select a girly and sexy outfit that incorporates all the elements of feminine clothing. If it’s your first time, don’t settle for a basic outfit – go all out! Try a mini bodycon dress that shows off your curves, and pair it with stockings and high heels or boots.


Best 10 Crossdressing Dares to Try


The most important element of your transformation is a nice, feminine wig. Choose a color that complements your style, but make sure the length is long enough to create a feminine look. Now it’s time for makeup. If you’re not sure how to apply makeup, you can follow a basic tutorial on YouTube, but don’t skip this step! Eyeliner, mascara, and lipstick can transform your look completely. To complete your feminine appearance, add some accessories like a necklace, bracelets, and earrings.


Wear Lingerie Under Male Clothing


Best 10 Crossdressing Dares to Try


This is the most fun and exciting dare for a beginner crossdresser but you’ve to be a little careful because you’ve to perform in public. All you have to do is wear a bra and panty under your regular male clothes and go out in public. Make sure the bra is not padded, it’s best to wear a sports bra because it’s more comfortable. The best place to perform this dare is an office or if you are a student then school. Make sure the male clothes are not transparent or reveal any bra and panty lines. If you are going to experience this for the first time it’s going to be very thrilling for you, nothing less than an adventure.


Wear  Maid Costume and Clean your House


Best 10 Crossdressing Dares to Try


Every crossdresser dreams of being a maid and serving a master. However, serving a master can be risky, but you can still fulfill your fantasy by wearing a maid costume and doing housework. You can buy sexy maid costumes online and pair them with corsets, pantyhose, a wig, and high heels. The shorter the dress and the higher the heels, the sexier you will look. Walking in high heels and a maid’s dress will give you a fantastic feminine feeling. Although tight corsets and heels can be uncomfortable, they’re also the most fun part of it, so don’t cheat and be an obedient sissy maid.


Learn Girl Strip Tease from Youtube


Best 10 Crossdressing Dares to Try


This is a dare not only for crossdressers but also for girls. Every girl secretly learns strip dance, twerking, or any other sexy move. To feel more feminine as a crossdresser, try challenging yourself to learn girly dance moves like a strip tease, pole dancing, or twerking. If you want to learn any other dance form, you can go for it but make sure it is girly and feminine. You can find tutorials online and practice until you get good at it. These moves can help you develop a more feminine figure and you will be able to adapt feminine gestures more quickly and easily. To take the dare to the next level, you can also wear the required dress for the dance and practice in it.


Paint your Nails


Best 10 Crossdressing Dares to Try


As I mentioned earlier, crossdressing is not just about dressing up, it’s also about doing small feminine things that bring you joy. This dare is about doing one of those things: painting your fingernails and toenails. It will make your hands and feet look pretty. If you don’t want to go out with painted nails, you can choose girly colors like pink, red, or light blue. But if you want to go outside with painted nails, you should choose darker colors like black and grey so that people won’t judge you. Beautiful nails are like therapy for your eyes and will instantly put you in a girly mood.


Get a Full Body Wax


Best 10 Crossdressing Dares to Try


This dare is a simple one that most of you can do easily. Just make an appointment at your local salon and get a full-body wax, including the bikini area. This is a very feminine thing to do and will make you feel more feminine. Smooth and clean skin will enhance your feminine appearance, and you will feel more confident as a crossdresser. Additionally, if you have a hairless body, you can wear revealing outfits like short dresses or bikinis. As a crossdresser, it’s a good idea to keep your body waxed regularly, not just for this dare.


Go Out in Public


Best 10 Crossdressing Dares to Try


Every crossdresser wants to show their feminine side to the world, but it’s also their biggest fear. If you are an experienced crossdresser but have never gone out in public while dressed, then you should take this dare. Trust me, it’s like an adventure sport as there’s always a fear of getting caught or being judged.


Best 10 Crossdressing Dares to Try


Before going out, make sure you practice walking and mannerisms that are feminine. Choose a decent outfit and avoid wearing anything too flashy or revealing. Don’t try to draw too much attention to yourself; just act normal, and everything will be fine. If possible, try to have a friend with you during your first public appearances to offer any necessary help.


Purchase Women’s Clothing Offline


Best 10 Crossdressing Dares to Try


This dare requires a lot of confidence since there may be situations where you have to interact with salespeople and come up with excuses to justify your purchases. If you’re buying dresses or makeup, you can easily say that you’re buying them for your girlfriend or wife. There may be times when you’re checking women’s clothes with feminine excitement  and the salesperson looks at you suspiciously, but it’s best to ignore it. If you respond or act strangely, it may cause a problem.


If you want to add more excitement to the dare, you can dress up in a feminine outfit and go shopping for girly clothes. It’s best to bring along a female friend who can help you interact with people at the store. As a crossdresser, this dare can boost your confidence in your feminine personality.


Do a Glamour Photoshoot


Best 10 Crossdressing Dares to Try


This dare is something that can create unforgettable memories. A glamour photoshoot is a great way to feel like a real diva. To do this dare, you can either find a studio that specializes in crossdressing photoshoots or ask a friend to help you out. I would recommend going to a studio because they will provide you with professional services, including dressing up and helping you with poses. Since crossdressing photo studios are professional places, you will feel comfortable and can do photoshoots without fear of judgment.


Post your Pictures Online


Best 10 Crossdressing Dares to Try


As a crossdresser, having a secret social media presence where you can interact with others as a woman is essential. If you haven’t set one up yet, I dare you to do it now and post your crossdressing photos. This will establish your online presence as a crossdresser and help you connect with others more easily. Crossdressers often receive lots of love and attention online, and if you’re lucky, you may even find a date. Make sure your makeup and outfit are on point so that those who don’t know about your crossdressing lifestyle won’t recognize you.




Best 10 Crossdressing Dares to Try


As a whole, it is crucial to approach these dares carefully and avoid taking unnecessary risks. If you are going out in public as a crossdresser, make sure to have a supportive friend with you to boost your confidence. Overall, these dares will undoubtedly enhance your love and enthusiasm for crossdressing, making it an even more enjoyable experience.


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