Wear a prom dress for 4 hrs, then the next morning for another 2 hrs like a bad sissy who stayed out and had to do a walk of shame. If you haven't got one go buy one from a charity shop

Do some grocery shopping while wearing a female version of a unisex piece of clothing. It doesn't have to be obvious, just needs to be made for women. For example: a leather jacket made for women, female jeans, etc.

Only female clothes when at home for the next 2 days

wear panties for a month

dare
 

wear a bra for 7 days straight.

I will be going to a city at the weekend

You will be fully crossdressing. You can start by going in all male clothes but take female clothes with you. You will go to a male bathroom and change into your female clothes where you will spend the remaining time in the city as a female

Each time you want to go out you have to wear female clothes even if under male ones but, you have to find a way to cum if you are not aloud into your panties at least, but if you can cum it had to be in your ass area and pulled up nice and tight.

If you don't have one, you need to get yourself a nice evening dress. You must try it on in the shop to be sure it fits. Afterwards go and have a Nice walk in your new pretty dress for 30 minutes you can choose the time and place you want to do it yourself but it needs to be done in 7 days. If you fail to do this within the time limit. You still have to do it but for a hour instead.

Going to the capital City of my country tommorow with a group of female friends of mine. They know I crossdress but eh they have mixed opinions about it.

Go to the city in male clothes (with panties underneath), then ask each of your friends to pick out one female clothing item to buy and change into. Wear the full outfit of purchased clothes for the rest of the time spent out.

Give me something sexy and challenging

Go into a busy shop wearing panties and a bra underneath your clothes. Make sure your bra is stuffed and king if noticeable and make sure your panties are visible at some point.

Can mine involves these clothes that I have: bra, panties, 2 thongs, pantyhose.
Not a dare outside though please

Give yourself a bra thong wedgie connection under your clothes for the day

crossdress
 

go to a shop in "male" clothes, leave with a skirt, go to a ally/toilets and change into it, go to another shop and get some tights, thats it.

something in a shop please

wear womens underwear (if you got)
then head to a shop that sells female clothes (or a shop that sells both male and female clothes)
try on 2 different women clothes, wheter you buy them or not is up to you

Dress up as girly as possible and watch a sissy training video and do everything you are told.
I have a bra, 2 thongs, a pair of panties and pantyhose.
No public or anal though.

Bumping the thread. Please include what I said above.