Wear a skirt and go out for 2h

Spend 24 hours completly dressed as a sissy

Get completely crossdressed. Put on panties, a bra, a short skirt, a girly top, makeup and a wig (if you can/want), stockings, and heels. Once you're satisfied with your appearance, go to a clothing store. Your goal is to find and buy a dress that matches your panties. (Only buy if money is no serious issue. If money is an issue, just find the dress.) Ask to try on any dress you think might match. Finally, as you check out, explain to the clerk the whole situation. If you're feeling brave, flash your panties at her.

Wow that a nice long dare you wrote there :)
I will give you something easy for you:
Get dreesed: skirt, panties, paint your fingernail pink.
And go for a 2 km run outside.
If you want you can put a buttplug.

Get dressed wearing a diaper and a pink shirt. You should take the diaper off to color on it, draw things a child still in diapers would wear. You shoul watch mlp for at least 2 hours, plus 30 minutes if you wet yourself.

Soak a pair of panties in water, then put them in the freezer. Once they're frozen, put five ice cubes up your bum and put the panties on. You may not take them off until the ice melts and the panties are dry.

Dress as a little baby girl with a diaper. stay full baby until u crapped teh diaper.

use my likes please :)

Transform yourself into a video game princess and let omegle interpret how you should be "saved"

Listen to sissy hypno files for at least 1 hour

Put on a bra and panties. Put an ice cube in each bra cup and three ice cubes down your panties. You may not touch your penis again until the ice cubes melt completely.

If possible, may I have a dare only within my likes? :)

Put on a bra connection wedgie, on top of that a thick diaper or a double diaper and a full female clothing set above that.
Now its time to go out, but you can hide it all under male clothes, take a bag with you though.
Go to some quiet area, like a forest or a park at night and put the male clothes in the bag. Now wet the diaper and take a walk of 2 km. You can put the male clothes back on after the 2 km and go home.

Wear your most padded bra and gag yourself with dirty panties, stay like this for 2 hours

Wear panties for the next X days.
Rolla dice to find X

Stroke your dick while fingering your ass. When you edge, let go of your dick and only stimulate anally. Edge 3 times. Try to cum like that

Insert your tail buttplug and act like a dog for 2 hours, eating/ drinking out of a bowl etc.