[BR1985]

Here’s a few for you:
Sleep naked - try and get up and use the bathroom in the night without dressing

Every time you use the bathroom after one of your friends give the toilet a good lick. Hopefully they’ll have splashed a bit.

Fill a bottle with your piss and drink it while infront of your friends. Bonus points if it’s a clear one. Do this while out on the slopes too. If really daring, refill the bottle while out.

Choose one day to give yourself a golden shower.

Try to spend at least an hour a day with your ass plugged.

Bonus dare - “forget” to pack any underwear (or maybe only something humiliating like tws or small briefs, giving you no choice but to go commando / wear humiliating underwear.