Hello Kyle,
Just a note to start: People don't usually put this much detail in dare requests. It's like you've planned out half the dare already lol.
The dare: Let's start you out with a simple one. (Since you mentioned diapers, I'm assuming you're into wetting, but skip those parts if you aren't.) First, go to whatever store you're planning to buy the diapers at. Ask an employee to show you where they are. When you go to pay, make eye contact and small talk with the cashier
Next time you go to the gym, wear your tighty whities and regular clothes but pack a diaper and gym clothes in your bag. When you change into your gym clothes, make sure you spend a lot of time in just your tighty whities, and bend over at the waist to show them off. Do your workout as usual. Make sure to stay hydrated, but don't pee.
Go to the sauna when you're done. I don't know what the sauna norms are in your area, but I don't think anyone will mind if you keep your embarrassing underwear on, right? Stay in there for a while.
When you're done in there, let out a little squirt of pee—enough that it might blend in with your sweat, but might not. Don't try to hide it, but you don't need to draw attention to it either. Make your way to the changing room, but change in this order: first take off your pants and underwear, then put on the diaper, then change your shirt, then socks, then finally put on your pants. If you're feeling daring, start peeing as soon as you have the diaper on, and don't stop till you're empty.
Best regards,
Winnie
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