10 Crossdressing Dares for Male to Female Crossdressers

Crossdressing dares are a great way to enhance your crossdressing experience and make it even more enjoyable and exciting. In this article, we have listed out some really fun crossdressing dares you can try for a great feminizing experience. For many crossdressers, it is quite common to stick to a certain routine of dressing up and then going back to their normal life. Dressing up in more or less the same manner and doing the same things repeatedly can be exciting at first but with time, it will start getting unsatisfying and dull.

To elevate your femme experience as a crossdresser, it’s important to not only dress feminine but also to adopt feminine manners and behaviors while you crossdress. This will make your crossdressing more exciting as well as help to build your own feminine personality over time. Before we get started with the crossdressing dares, please keep in mind to avoid taking unnecessary risks, follow the law, and only try out the dares which are comfortable for you.

Here are 10 Best Crossdressing Dares to Try Out for Male to Female Crossdressers:

1) Wear Lingerie Under Your Male Clothing

This is a fun crossdressing dare to get started with, especially for beginner crossdressers. Wear a comfortable bra and panty (also pantyhose if you like) under your male clothes for a whole day while doing your normal routine like going to work or college. This is a great way to feel girly without having anyone else know about it. It’s fun and exciting when you are wearing lingerie secretly inside your male clothes. This will also give you an idea of how girls feel wearing their lingerie (undergarments). The best place to perform this dare is in a place where there are going to be many people like an office or college, malls, clubs, coffee shops, restaurants etc.

Wearing lingerie under your male clothing is also a comfortable way to introduce yourself to crossdressing in public without taking bolder steps. When you wear a bra and panty under your male clothes and step out in public, you become more conscious about what you are wearing underneath. It will give your body a powerful sensation of femininity.

While performing this dare, you will need to be a little careful not to expose the lingerie that you are wearing. If you don’t want to take any chances of being caught while doing this dare, make sure that the bra straps or panty lines are not visible under your male clothing. Also, don’t wear padded bras, or clothes that are too tight or too transparent, which reveals what you are wearing under your clothes.

Check Out – Lingerie for Crossdressers

2) Do a Full Body Hair Removal

Having facial and body hair is a big NO for women. This is why women regularly shave off or wax off any excess hair on their bodies and face. Having smooth and clean skin is considered a feminine thing. So, for this dare you will need to get a full-body wax or shave off all your body hair and facial hair. Removing all the hair from your face and body will instantly enhance your feminine appearance and will also make you feel more feminine. It will also feel great to wear short outfits and a bikini that shows off your new smooth, hairless body.

Nowadays, many guys also prefer to have smooth, hairless body. So, it won’t be awkward to go to your local salon or beauty parlor and get a full body wax. If you prefer to do it yourself, you can easily do it at home using body wax or shaving kits, or Hair removal creams. Make sure to clean and moisturize your body after removing all your body hair. If you want to undergo permanent hair removal, you can try Laser hair removal.

3) Do a Full Body Male-to-Female Transformation

This cross-dressing dare is a must for anyone who wants the ultimate feminine experience of being a lady. For this dare, you will need to dress yourself up completely from head to toe as female and only wear items and clothes that are associated with femininity. A full body male-to-female transformation should include feminine undergarments, a nice hair wig, full facial makeup, a sexy dress, breast forms, high heels, feminine perfume, some accessories (earrings, necklace, etc.), and a nice handbag. Once you do a full body transformation, you will realize the full potential of your feminine self and experience the wonderful sensation of being a woman.

Here are some steps you can follow for a Full Body Male-to-female Transformation:

1) Take a nice shower. Shave/remove all your facial and body hair.
2) Moisturize your face and body properly.
3) Put on a clean, sexy bra, panty, and sheer pantyhose.
4) Put on breast forms/breastplates for an attractive feminine appearance and feminine sensation.
5) Wear a sexy dress (bodycon dress, LBD, floral midi dress, etc.) that fits you nicely.
6) Apply Makeup – Foundation, mascara, eyeliner, fake eyelashes, lipstick, blush. Paint your fingernails and toenails (Optional – wear Press on nails).
7) Put on a long, thick, and stylish hair wig.
8) Wear accessories – Earrings, necklaces, bracelets, a watch, and a nice handbag.
9) Put on high heels.
10) Splash yourself with a feminine fragrance.

After your full body transformation is complete, make sure to take plenty of photos and videos in stunning poses.

Check Out – Breast Forms for Crossdressers

4) Post your Photos Online

This is an easy dare but at the same time an exciting one. With the rise of so many social media platforms, it’s so much easier for crossdressers to now connect with other crossdressers/admirers or just other regular people. If you like receiving attention from other people or want to expose yourself, then this dare is perfect for you.

Take some nice photos of yourself in your favorite outfits. Create a new profile as your feminine self on different social media platforms like Facebook, Instagram, TikTok, etc. Add or make new friends and also join some groups. Next, post your photos (or even your videos) and share them with your online friends. You can also join different crossdressing groups or just regular ones and post your photos/videos there for other people to engage.

Having a secret online presence where you can express your feminine self and interact with other people can be both fun and exciting. You can also pretend to be a girl/woman and interact with other people. It’s quite exciting to get a reaction from others to your photos/ videos and be treated as a girl/woman. When people engage with your photos/videos, you will feel a sense of thrill and excitement of being exposed as your feminine self.

If you don’t want to reveal your true identity, take caution by not posting your face or photos of you in your room or places which make your identity obvious. Once you upload your photos or videos online, there is no going back because it can reach a lot of people with or without you knowing. Someone else might simply download your photos and post them somewhere else. There is always a chance that someone might recognize you or your background if you are not careful. So, if you want to maintain privacy, make sure not to upload any photos or videos that jeopardize your identity or situation.

5) Go Shopping for Women’s Clothing & Items

While shopping online is fun, going to actual stores to buy feminine clothing and items is a lot more exciting and rewarding as a crossdresser. So, for this dare go shopping for women’s clothing or items at local women’s stores around you. This will be quite fun and exciting since you will most likely have to walk around the store to check out different items and also interact with a sales person in the store.

If you want to make this dare even more exciting, you can shop for lingerie or sexy high heels. You can also wear sexy lingerie under your male clothing while you visit the stores. If you are comfortable and confident enough to crossdress in public, you can even go shopping as your feminine self wearing a nice feminine outfit.

If you are new to shopping for feminine clothing or items at stores, you might find this dare a little intimidating at first. But once your try out this dare, it will really boost your feminine confidence and you will feel happy after this wonderful experience. Sales person in stores are actually quite friendly in general and while interacting with them, you can admit that the purchase is actually for yourself. If you don’t feel comfortable or nervous interacting with them, you can just mention that you are buying of looking for clothing or items for your girlfriend or wife or for someone else as a birthday gift.

When you visit the women stores and browse through the items, try to stay calm and don’t rush. Take as much time as you need while shopping for the right items for yourself and don’t worry about what other people might be thinking about you. Just have a nice time shopping for yourself.

6) Do House Chores while Fully Dressed

Doing house chores is a lot more fun when you are dressed feminine and beautiful. This dare will help you experience how most girls/women feel while doing chores in the house. For this dare, get dressed in your favorite feminine outfit or a nice dress, put on hair wig & makeup, pantyhose, and wear a nice pair of women’s shoes (high heels make it more sexy). If you want to dress up as a maid, you can get yourself a pretty maid costume for this dare.

After you are fully dressed, start doing the housework with all the curtains of the house fully open if you want to make it more exciting. You can start with vacuuming all the rooms, cooking food, taking out the garbage, cleaning the dishes, doing laundry etc. After completing all the chores, give yourself a nice treat as a reward.

Check out – Maid Costumes for Crossdressers

7) Crossdressing in Public

This list cannot be complete without this dare. Crossdressing in public is one of the most exciting and liberating thing you can do as a crossdresser. This is a great way to show off your feminine side to the rest of the world and also validate your feminine self. Stepping out as a woman can be quite challenging and scary for many crossdressers because of the fear of getting caught, mistreated or judged by others. But if you are careful enough, do a good planning and if it’s safe for you to crossdress in your country, you will realize how wonderful and satisfying it feels being outside as your feminine self.

So, try out this dare if you have never went out in public fully dressed. For your first outing, you can plan a short trip to an area where there is going to be very few people or none at all. Avoid very short or tight outfits, high heels, flashy or revealing outfits, too much makeup, and cheap hair wigs. Try to blend in public by wearing a simple outfit that girls/ women around your area normally wear. Make sure you are not overdressed and first feel comfortable with your feminine appearance before stepping out. Avoid crowded and risky place for your very first outing.

The best way to crossdress in public for the first time is to go out with a friend that supports you. It’s also a good idea to practice your feminine manners and walk before venturing out. Once you are ready for your first outing, wear a nice outfit that matches the occasion and timing of your outing. Also, don’t forget to carry a nice handbag to carry some money, your identity card, mobile, keys and some makeup items to touch up if needed. Avoid taking unnecessary risks and try to stay calm and composed. The main idea of crossdressing in public is to have fun and just enjoy your feminine experience. So, go out for a nice walk or a short drive and gradually go out for longer time as you get more comfortable.

Check Out – Tips for Crossdressing in Public

If you are an experienced crossdresser who has cross-dressed in public few times, you can try out the following things:

• Go to the movies with friends.
• Go to a nice coffee shop or restaurant.
• Go to a nightclub with friends.
• Go for a long drive and stop for gas at the gas station
• Go shopping at the mall.
• Do grocery shopping at your local departmental store.

8) Role-playing as your favorite female character

Another fun dare to add some excitement to your crossdressing. Role-play as your favorite female character and try to stay in character for as long as you can. Roleplaying is a lot of fun because you can be whoever you wish to be. This is a fun way to fire up your imagination and allow you to explore parts of yourself you didn’t know existed before. You can dress up as a sexy secretary or a beautiful bride or a cute waitress or anything else you want. It will also help to make new decisions and improve your impersonation skills to behave more feminine.

Check out – Costumes for Crossdressers

9) Paint your Nails & Toe-Nails

When it comes to crossdressing, it’s not only about dressing up but also embracing a feminine lifestyle. One of those things is painting your nails and toenails, which is a very feminine thing that you can do. So, for this dare paint your nails and toenails with some lovely nail polish. It’s fun, relaxing, and a great way to boost your girly mood. It will make your hands and feet look cute and stylish. You will feel feminine, confident, and attractive when you paint your nails. Try out Press-on nails if you want to feminize your hands even more. You can also visit a beauty parlor or saloon to get a manicure and pedicure and get your nails done professionally.

10) Visit a Crossdressing Studio and Get a Professional Makeover

This dare is a must-do dare for crossdressers who want to look their best and have a glamourous makeover in-front of other people. This will be an unforgettable feminization experience for you. There are crossdressing makeover studios in many areas nowadays which caters to crossdressers and Trans women.

In these crossdressing studios, you can choose from many professional services like a complete makeover package, glamour photoshoot, full-day outings, wardrobe service, personal shopping, makeup lessons, and much more. It makes a huge difference when you get a transformation from professionals who knows what they are doing. Many crossdressers admit that getting a professional makeover has been life-changing experience and they couldn’t believe how beautiful and passable they looked after getting a full makeover.

Even if there aren’t any crossdressing studios near your area, you can try out regular beauty parlors or saloons. You can even hire a professional makeup artist to give you a full makeover at your own home. So, find yourself a nice makeover studio near you and get yourself a full body makeover service. Don’t forget to include a glamour photo shoot and personal outing experience afterwards if possible.

Check out – List of Crossdressing Services

We hope you enjoyed this list of Crossdressing dares. Do let us know how many crossdressing dares you have completed from this list in the comments below.