I started by just taking off all my clothes I was wearing anyway and folding them nicely and placing them on my bed. It was my university hoodie, a black long sleeve shirt from H&M, black adidas windpants, a pair of white socks, blue converse shoes and black boxer briefs.
I decided to start with the most valuable item first to get it out of the way, I really don't want to have to destroy my shoes (in fact, kind of cheating, but knowing my pussy self I suspect that I would've quit the dare if I had to destroy them so if you're reading this I didn't roll a 1). I rolled a 5 for those so I get to bring my shoes.
I figure I'll just work up from the bottom, so next is my socks. Rolled a 1. Luckily I have lots of socks so wrecking one pair doesn't really matter. I tried just ripping them but they were too stretchy, so I grabbed some scissors and cut them from toe to ankle. Into the garbage they go.
The adidas windpants next. I'd be sad if I had to destroy these since I love em so much and they're hard to find. Luckily rolled a 6. Woohoo!!
Black boxer briefs; rolled a 4.. okay fine, easy then.
The shirt: a 3. Almost had to go shirtless but it's looking like i'll be a fully clothed person, at least on the way there.
Finally for the hoodie I rolled a 4. So only had to destroy the socks.
There's a kind of hilly field outside of town between the town centre and the highway with a water tower in it, so I'll head there. I'm going to have to park on the side of the road so hopefully I don't get a ticket doing this. I already had to pee before I left but I drank a whole water bottle on the way anyway.
Aaand I'm back. Jesus that was cold.
I went into the slight brush/woods at the edge of the field with the water tower. I felt that I could definitely carry my shoes to my car and drive barefoot, so I took those three minutes off right off the bat, setting my timer for 57 minutes.
I didn't think it through, but October in Canada is not the time for this sort of thing. It was so cold that at first I had a hard time keeping a boner. The predicament made me horny enough to overcome this after about ten or fifteen minutes though. Maybe the shivering helped my masturbation technique.
I knew I was going to have to pee, but because of how cold it was I seriously considered taking the ten minutes off by pissing on all my clothes. I figured that would make it even colder though, so just did the five minute one; pissing into my cupped hands and down my legs.
This warmed me up for all of thirty seconds, and then was absolutely FRIGID. The piss cooled so quickly and started wicking away the little body heat I had remaining.
By this time I had about 30 minutes remaining, and wasn't sure if I could really finish. I wanted to push through though because I rarely do these extravagant dares and was finding the situation really hot (despite it being physically cold). I've been thinking lately that I want to unleash my inner slut, but I always bitch out, so finishing this dare was one opportunity to prove to myself that I could do it.
Either way, I really had to get more time off, I was shivering and it seemed pretty unlikely that I was going to cum. I decided that I'd take 6 more minutes off by risking my shirt and my boxers.
I dug through my windpants pocket for my wallet and got a quarter out. I flipped for the shirt first and got heads. I put the body of the shirt under my feet and stretched the arms behind my back over my head until they started to rip. When they did finally fail, I almost fell over I was pulling so hard.
Then I flipped tails for my boxers. To be honest, I was kind of dissapointed. A big fetish for me is trashing underwear and being stuck going commando, especially in windpants. At this point I was pretty horny and down to destroy them, so I figured I'd take time off by continuing to flip until it came up heads.
This strategy only ended up taking off another three minutes, since it came up heads right away. I put my fingers through the fly of the boxers and stretched them as far as I could, ripping them open. The material came off of the waistband in the front but stayed on in the back. I ripped the waistband off the whole way 'round.
I was finally able to cum after that. I looked at the shreds of my underwear and knowing I only had windpants to wear, I came on the shredded underwear.
I kept stroking for the last ten minutes but didn't get hard again. My body was rough with goosebumps and I was really freezing.
Nobody came by during the whole time, guess I picked a good spot.
When my phone read 9 minutes remaining I was done. Pretty relieved, I pulled my windpants up (without underwear on
), put on my hoodie and carried my shoes back to my car. The pants got damp with my piss which hadn't dried yet, and I smelled kinda terrible. I brought the shredded boxers and shirt with me, don't wanna pollute!
I'm really glad I didn't have to destroy my shoes or pants. With my luck I expected that I'd end up losing them. The public stuff was fun, I wasn't sure about the spot but I guess nobody has any reason to come into the rough edge of a field outside of town. I do think I'm going to have to clean the pedals in my car though, my feet were kinda pissy when I was driving barefoot.
A fun dare! Glad I did it, I never go through with these kinds of things so I'm impressed with myself. I think I'll do more in the future since it's really liberating to do this kind of risky stuff despite my qualms.