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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.

    1. I am a jegging legging boy, I wear them everywhere and love the feel, most always with a gaff and hose and I would not change,
      You have to do it right though , you must shave the bod completely, or have the laser remove the unnecessary hair, stay firm , work out , stay tanned year round, do the nails, get the anklet , enjoy yourself.

  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

  10. I have done everything on this list at one time or another, some with great regularity. Others only once or twice.

  11. Yes, i do all of them, except last two points, and is fantastic.
    What i really like, is to massage the skin with parfumed cream before dressing, and spray some parfume in the right places…

  12. I have been crossdressing since I was 14, I am 60 now. I have done the whole thing with makeup nails heels and long wigs. I love tight dresses and mini skirts stockings ,bra and panties even have a few garter belts. I have a few friends that are into having me dressed up around them, and it feels so good when I get dressed a little slutty and they tell me how good I look . I wish I could live as a woman all the time!!! I know that I would be a good sissy slut for the right guy 😍 or guys 💅👠👗👙👜👄

  13. I absolutely love this list, I’ve already done some of these things but now I’ve got more to do. Thank you sooo much, I’m really looking forward to this. 💋

  14. On the closet crossdresser not very brave but I am wearing panties now and I’ve got my toenails painted and I bought a lipstick that is very difficult to get off enjoying it so far

  15. I dress and go out and have sooooo much cum I mean fun. OH love being a girl I dress every day and always every day i wear panties and most every day I wear my bra- My favorite dress is to wear a very short mini skirt and advertise to all men I am ready to make you happy very happy in many many ways. Love being girl soooo very much and pleasing men sooooo very much

  16. One dare to try is using the ladies room. It was one of the most incredible feeling, knowing that you are in a place where there are only females.
    My first time going to the ladies room was when I was at a outdoor shopping center and needed to releave myself. I found the food court and saw a sign that said Ladies and a arrow pointing to the hallway at the side of the food court.
    I went down the hallway toward the entrance and was surprised when I saw that there was just a doorway without a door.
    There was also a line of women and girls waiting to go in.
    I stood behind a girl and watched as one girl would leave, one girl in the line would go in
    Eventually I was the next one to go in, and when a girl came out, I went in
    My heart was racing as I stepped through the doorway and saw two lines of stalls, on each wall. There was 10 stalls on each wall. I began walking down the row of stalls and they were all occupied. When I got to the last one I turned turned and began walking back on the other side of the ladies room. I found a empty stall and went in and closed the door behind me and locked it. I was trembling in the stall, when I heard the unmistakable sound of a girl peeing in the stall to my right
    I knew that I had to make that sound like she was, or taking a chance to being outed.
    Luckily I was wearing a prosthetic vagina that directs the flow of urine into the middle of the toilet bowl, so it would make a sound like a girl would who is peeing.
    I hung my purse on the hook on the back of the stall door, then pulled my skirt up and pulled my panties down, and squatted over the toilet.
    I released my bladder and began peeing. It sounded exactly like the sound that I had heard in the stall next to me.
    My shoes were pointed in the right direction and my panties were down below my knees as I was squatted there peeing.
    When I was through, I wiped myself and pulled my panties up and my skirt down.
    I stood up and flushed the toilet and taken my purse with me, I opened the stall door and went to where the sinks and mirrors were.
    I washed my hands and touched up my lipstick, then walked out of the ladies room
    Since that first time, I’ve used the ladies room many times without having a problem.
    Some are easier to use then others. The more stalls there there are, the easier it is to get in and get out.
    Just don’t get into a conversation with any anyone. Just go in and do what you have to do, and leave

  17. Tip No. 2, wearing panties under my men’s clothing, I’ve been doing it for a long time, accompanied by a padded or non-padded bra depending on the risk of being hunted based on the outfit of that day. Another outfit that I add is pantyhose, although I have to be careful so that my pants don’t slide down, tightening the belt more. Another complement to feel feminine is to add a pad to my panties. The truth is that I felt great. Thank you.

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