dress up like a woman and then ask the person you're chatting with to make you do something. you must complete it before they disconnect. complete 5 of these before you can stop

crossdressing is out of my limits.

Then for both of you,
Wear only a thong, and a towel. Then talk to someone. Try to place a bet with them. He can choose if your wearing underwear or not. When he has picked. Show him ;-) try to win something by winning the bet and promises to do something when losing the bet.

Well since you do like crossdressing...

i dare you to dress like a female and once you can get someone talking to you longer than 2 minutes, show them your dick
do this at least 8 or 9 times

lol, try this on gay chat roulette, it's even more fun :)

get on chatroulette naked with "dare slut" writen on your chest, you may not leave or put clothes on until you have both seen someone cum and had someone else watch you cum, must do any dares they give you if they happen to read your chest

log on to either chatroulette or omegle. Strip naked in front of the cam, regardless of who is watching. Don't disconnect from anyone. Present your body until someone stays on your cam.

If it's a male: make him cum by teasing him with your tongue and mouth
If it's a female: Offer her your obedient services as long as she desires

The task is complete, either when the male stranger cums due to your teasing or when the female gets tired of playing with you.

If you're male: Strip naked and get a boner on omegle and stand up straight till the boner fades away.

If you're female: Strip naked on omegle and fondle your tits for 30 seconds to the cam.

Pretty simple for you...

Start a 30 min session on omegle.
For every female stranger you're getting connected too, remove one item of clothing.
You are not allowed to get dressed, until your 30 mins end.
And you are not allowed to disconnect anyone.

Have fun.

u must do anything and every thing a person asks u to do.

put a dirty gag in your mouth while holding a sign saying you will be anyoes slave for 30 min cant take gag out till been slave for 30 min or 3 hours

ask to be everyones slave until someone says yes and you must do ANYTHING they say

show your penis. no nextign. and must stay like this for 1 hr

Sit naked, but place the camera so its ass level and only gives that view. No nexting for 30 minutes, if anyone talks to you offer to show them anything they ask for.

do your pose in your profile thing and then no nexting. sta like this for 1 hr. if anyone wants to see more then let them