This is an epic dare, pun intended. I'm gonna report below, so obviously I tag it a spoiler as it reveals options. Also, I considered a pint to be about 450ml and a cup 250. I used a measuring cup.
Spoiler:
Ok, one pint down.
1. I head to the bridge. I'm not even going to talk about the club pun XD but I didn't wet my pants with tap water because I wore no pants and found it a bit pointless at the moment - feel free to punish me tigerclawz. I then waited because apparently I'm DUMB, and finally did C. So at this point, 1 pint and 15 minutes in.
2. Charged the troll. I guess 1. didn't cure my dumbness. Being a greedy bastard I also tried to loot everything, before finally filing an application to the (GIGANTIC!!!) troll club. 2 pints, 1 cup, and 20 minutes in. Not counting the reading and decision making of course.
3. Felt lucky: I borrowed the unicycle. It worked out. Nothing to see here.
4. I got good balance. But overall, between that minute and the reading, we're probably at 2 pints, 1 cup, and 25 minutes.
5. I begged for a lift. What an idiot, I actually thought I could drink fast enough - because frankly I had no idea and thought, why not try? I downed half a pint in 8 seconds, so I failed, AND waited 30 minutes. That's when I began feeling really uneasy. I wasn't needing to pee yet, but I could feel the dripping filling up my bladder, very fast, teasing it. 2 pints 1/2, 1 cup, 55 minutes.
6. I think I'm way too naive to deal with leprechauns. I really was trying to not pick the idiotic stuff, but I thought it was the last one. If only I had thought about the author's name... Long story short... I did them. ALL. In order. Rock, paper, scissors, and fuck you. Five slaps on the wrist later, We were at 2 pints 1/2, 2 cups, and 1 hour.
7. At this point I was hoping there would be toilets in this town. Why didn't I let the brawlers be? Thinking that getting in the fight would make me lose my gold, I just reported them. Maybe I was hoping for a reward, I don't even know in fact. I got robbed and the mob forced-filled my bladder even more. Aside from the humiliation, we're at 3 pints 1/2, 2 cups, and 1h30.
8. I was desperate. This was getting painful and I had to stop doing whatever I was doing and hold it all through those 30 minutes. This is when I started counting down the questions left. I picked the skipping rope but hadn't any proper ones, I used a piece of cloth that was lame and failed after a dozen skips. I thought, since this isn't an actual rope, let's also forget about the cup of water - it's like it hadn't been an available choice in the first place. If that counts as cheating, again, feel free to punish me. I was just trying to make it fair. Which it wasn't supposed to be anyway so I'm just going to shut it. Afraid to be asked to juggle, or to drink, I picked the nipple clamps. Yeah, I was strategizing the whole shit at this point. Strangely enough, and despite my nipple agony, it wasn't hard to hold it while I was jumping around like a ridiculous jester. Actually I'm not even mad, I was a pretty cool jester. Cool naked jester.
9. Those morons took 15 minutes to write down my name. No I don't even have anything to say. Except, 3 pints 1/2, 2 cups, 1h50 or 55.
10. I was talking to myself, forbidding myself aloud to pee, and bending over with moans and grunts several times each minute. "You could really use a loo at this point, right?" Dungeon masters are fucking sadists. Still trying to optimize the shit out of every opportunity, I asked the beggar (lucky me!!!) and there you go.
11. I'm way too kinky for my own good and picked the monastery. Seems like the easy way out right? Not for a slut like myself. 24 hours denial?? I practically spend every of those jerking off these days! I currently don't have an ounce of chastity in me. I fucked off to the tavern. This was pathetic. I had a 15 minutes wait first, because my sluttiness both led me to the monks first AND prevented me to pick them, PLUS 15 minutes doing the damn dishes because of course I was robbed by the mob who decided earlier that because I snitched on them, I would piss myself.
This is where I began to fail. Yeah, that close to making it.
At 3 1/2 pints, 2 cups, and 2h, I wet myself. Wet, because it was enough to make a puddle. But I took control back a few seconds later, I had only made a small puddle (I guess, 1/4 of a glass?) and kept holding. I was feeling much better. It lasted 10 minutes. At this point, after holding back very few waves of desperation, I wet again. Definitely half a glass on this one. Time for the dishes. Having my hands immersed in warm water was the worse part, except if you count the splashing. I never knew before that having droplets sprayed on my bladder could make me need to pee so badly!!! Between 10 and 5 minutes to the end, I wet again, soaking the floor. It was like I had dumped a whole glass on the ground. And it was so few compared to what I was holding. My bladder was still bulging awkwardly and I whimpered pathetic little moans while I forced myself to stop.
I finished the dishes part and was finally free. I was standing naked in the kitchen, with three humiliating distinct puddles of different sizes on the floor. I don't know if this dare is very, very well devised, or if it's a coincidence that I lost it at that point, but either way this was both a good read (sometimes actually hilarious) and a really good dare. I only wish the desperation relied more on drinking than waiting because that's not really something I like, but that's just me so I guess this is just an amazing game. Now if you'll excuse me, I have to go mop up my shame.
Oh, and if my wetting means I failed the dare, I guess this is a third reason for punishment. I'll let the sadist decide if he comes back, otherwise I don't know. But for those who don't want spoilers, do it, you'll have fun and your pants probably won't survive dry.
Edit: I forgot to tell that now my bladder has been destroyed like this, I run to the bathroom every 15 minutes. And not just from the remaining water and the fatigue, I actually almost wet before I realize I'm desperate. I hope this comes back to normal in less than a day (it's usually how long it takes) because I have to go out tomorrow...