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Crossdressing Dares to Try – Complete Feminization Experience

Crossdressing dares to try

If you are a crossdresser who has been crossdressing for sometime, you probably know that it can start to get boring doing the same things you do after dressing up every time. Every crossdressers wants to experience different feminization experiences, from looking fabulous to going out in public as a woman. Our list of crossdressing dares  will certainly bring out the woman in you and make your crossdressing experience quite exciting and fabulous.

No. 1) Get Dressed from head to toe.

You haven’t really experienced a full feminization experience until you have completely dressed yourself up from head to toe in  feminine attire only  that includes feminine undergarments, clothing, makeup, heels, hair wigs and other accessories.  For this crossdressing dare, you will have to leave all your male things behind.


Start by undressing yourself completely. Then, wear a lovely bra and knickers. Then put on a nice dress or any femme outfit you have. Next, put on a nice hair wig. If you have long hair, you can just brush it and give it some lovely style. After this, you need to put on some nice makeup on. Make sure you don’t miss out on applying eye liner and lipstick.

Now, your transformation is almost complete. Its time to add more details into your appearance. Put on stockings/pantyhose if you like. Then, time to put on some nice heels and wear accessories like earrings, necklace and bracelets. Finally, carry a nice purse to hold. Now, you are properly dressed from head to toe. Enjoy your complete transformation in your feminine avatar and make sure to take lot of photos and videos.

2) Wear panties inside your male clothing.

This can be fun and interesting experience for crossdressers. If you have never done this, it could be a very thrilling experience for you because there is a certain chance you can get caught if you are not careful. So, you will be more conscious when you are wearing female underwear inside your pants.

crossdressing in panties

So, pick a nice girly panties o wear. Then go out and do your usual things wearing it all day and even whole night if you want. This will certainly get you an idea of how most girls feel in their underwear. If you want to add more thrill, you can also wear a bra too. Padded bras are straight giveaway so if you don’t want others to know, better wear tight sports bra or bra’s without heavy padding. You can also wear pantyhose. Especially in winter, it is much easier to wear feminine dressing inside male clothing.

3) Wear High Heels while doing House Chores

Walking on high heels brings out amazing feminine sensation to your body and mind. Your posture is also altered to a more feminine structure while standing and walking.

Crossdressing in high heels (2)

So, put on a nice pair of heels and finish all your house chores like cleaning the dishes, vacuuming the rooms and taking the garbage out while wearing a nice pair of  high heels. If you are more bold, you can also dress up fully or just wear some other feminine clothing or item with your heels.

4) Do a full body shave or hair removal

Girls and women usually shave off all their facial and body hair to make their skin look  clean & smooth.  Guys on the other hand have more facial and body hair and don’t generally shave it. For this crossdressing dare, you will need to shave off all your facial and body hair.

crossdressing in pink dress

This will certainly give you a lovely feminine sensation and will be a nice experience for you. Your overall appearance will also look quite feminine and the clothes you wear will also feel different in your new smooth hairless body.

5) Paint your fingernails  and toenails

Another very fun and girly thing to do is to paint your fingernails and toenails with lovely nail polish. This will make your hands and feet look pretty & feminine. You will also notice that it  has strong visual effects and will make you feel more girly & cute.

crossdressing - putting on nail polish

Paint your nails with some nice bright colors like pink, red or orange to create a more brighter look.

6) Wear a bikini or swimsuit

Bikini & swimsuit is one of the most feminine things that you can wear. When you wear a bikini, much part of the body is exposed and you will feel more conscious  about your appearance. So, put on  a sexy bikini or bathing suit and see how your senses tingle with femininity.

crossdresser in swimwuit

7) Roleplay

Roleplay is a great way to add thrill to your crossdressing. For this dare, you can just roleplay as your favorite female personality or your favorite getup like a school girl or a secretary. Dressing up as your favorite female character will give you a great sensation about your feminine side. This is also a nice way to improve your impersonation skills to learn to behave more feminine.

crossdressing roleplay

8) Post your photo or video online

Many crossdressers like to see how other people react to their feminine looks. There is certainly a lot of  thrill when you are exposing yourself to others. Its an exciting feeling to know people are looking at your photo and they have now seen you as a girl/woman.

crossdressing pics

So, for this crossdressing dare, you will need to click a nice photo of yourself. If you are very shy, you don’t need to show your face. So, after you have a nice photo, create a new profile as a female in social medias like Facebook, Instagram, YouTube or CD forums, then connect to some crossdressing groups online and post your pic or video.

9) Order food & receive it as a girl

This is another exciting crossdressing dare to do. You can order some food or items online and then when the deliver guy comes, you can receive it dressed completely as a girl/woman. For this dare, you will need to be a little more confident. But this is really a very fun experience to try out.

taking delivery as girl

10) Go Out in Public

You must have expected this one on the list. Of course, going out in public is the ultimate dream for most crossdressers but at the same time quite scary with the thought of being exposed completely and people finding out. You will definitely need to do some practice on your dressing & transformation skills before venturing out.

Crossdressing in public

So for this dare, you can put on a nice outfit that matches the occasion and time ( don’t wear very flashy & revealing outfits on your first time) and apply some proper makeup and head out.

Make sure to carry a purse with some money, your identity card, keys and your mobile. If you want to avoid people, going out early in the morning or late at night is better.  If you have an understanding friend or partner, you can go out with them together. This will make you feel more confident and safer.

Hope you liked this list of crossdressing dares. If you think we missed on any nice dares, please let us know in the comments below. Thanks for reading this article. Have a great time crossdressing!!

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  1. Thanks for the list. I am going to try all these and let you gals know how it went.

  2. I have done everything except for painting my toe nails and I must say it is sooooo nice to be totally dressed as Michelle.It just feels right.

  3. 1st went out when a friend remarked that going to a gay bar was just an extension of the closet.Nothing beats going shopping ,dining out etc. as a woman.Of course there is a huge fear factor but most of it is self induced.
    And 1 item that is seldom mentioned in articles re: going out is the ladies room.
    Attend a play etc. and stand in line at intermission for the ladies. Be sure to touch up your lipstick at the mirror too. THAT is the ultimate test and pass that and when you go out subsequently you will be fearless and start to think of yourself as a lady doing women things

  4. I have been crossed dressing since 97. My late wife started it. I am totally shaved all the time. I only wear panties
    I was caught by a female x-ray tech. One of the images my pants needed to dropped between my hip and knees. She came to position me. She pulled my pants down. She got red. I didn’t even flinch. Baby blue panties, shaved legs and pubic area. She got the shots. She came back. Due to my back problem, she had to pull my pants up. I apologized for her having to do that.
    She asked me out on a date for Saturday. I told her I must be twenty five years oldér. She gave her name and number. I gave her my femme name also.
    I would walk with two inch the theater. Apartment door to theater ninety yards. I go to afternoon showing Two pizza places,, chicken, or pancake place. They were not to far out of the way

  5. Great information, I found it very informative and look forward to following some of your recommendations.

    Thank you,

  6. Check into a motel en femme. When they do a double take on the name on your ID, tell them your femme name as well. If they note it on the registration, the people who check you out in the morning will call you by your preferred femme name (at least that’s what happened to me the one time I was brave enough to do it).

  7. I did all that in one night, I spent several months preparing my mind and foreseeing how it would be, where would I go. During that time I bought all necessary garments and accesories to look like a sexy woman.
    I’m hairy, I decided to completely shave from waist down, and I got a turtle neck long sleeves pullover. To hide my hairy hands I got too a pair of cute gloves.
    Make up, lipstick, earrings, long hair wig, feminine glasses (to get a secretary look).
    Stockings with non sliding lace, a thin tight pencil miniskirt with a short bikini (I like people to notice my underwear), and 5 inches heels.
    At the night club I tried not to walk, I really dont master heels sexy walking (yet). But the results for that memorable night were more than satisfactory.
    I’m eager to repeate the experience, I just need the club to re-start activities.

  8. Love dressing as a woman. It is so amazing to experience being a woman.

  9. i’ve done most of these before reading your dares, most order food not done that yet, i have been out once at midday fully dressed as a woman makeup, heels , miniskirt, i felt so girly it was fantastic

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