that sounds very interesting, i've always wanted to be in a situation where i'm crossdressed with no way out. how did you do it?

I went to a park where I know the trails well. It is an island in the middle of an urban area. I have done many things here before, but never something quite this risky.

It was fairly late, but not too late (before midnight). There is a spot on the front, SW corner of the island where I put a key near a fallen tree. I then went abut 1 mile to a pier on the NE side. I stripped COMPLETELY naked. Took a cable bike lot out and threaded my shoes, underwear, shorts, shirt, onto the cable and took out the lock, and hooked it on.

I knelt naked, by the pier, next to my clothes and started to adjust the lock so I could close it. I totally hesitated.

About three minutes I ran through my head all sorts of scenarios. I listened. I glanced around. I shivered. Then the cable slipped a bit and I became unsteady, and I gripped the lock and it clicked.

Now...no turning back.

First, I was stunned. I replayed the sound of the click. I tugged on the cable. I tugged on my clothes.

Naked, no hope but the key.

Wow, I love being naked.

Barefeet on the muddy trail. Breeze touching each part of me. Penis bouncing with each step.

Heart pounding.

Then I came to the first open area. It was decently lit and viewable from the shore.

In order to check on how risky this was...I would have to step out into it. This area is also, somewhat viewable from shore.

I took my cock and balls in my hands and stepped into the light.

I had to be quick...ish here and yet, barefoot, there was gravel and garbage about so I had to watch my step.

So, I am naked. Holding my package which, though limp, is leaking in my hand. To keep it covered, I am slightly bent and totally NAKED.

In the middle of this 100 yard lit area, I hear a “hey” from somewhere.

Who knows. Everything echoes here, I try to convince myself. I see a little light on the far shore, moving. A bicyclist.

Looking slows me up so I bolt, lightly on my barefeet towards a tree line and the trail there. Again, bent and doing the nudie hop step.

To the tree line. I hear something else, but I am covered.

If they come back over, though, I have to cross that area again.

My hands are covered in precum. It is dark enough, though, I don’t cover up.

There’s the key spot.

A little feeling around in the mud with my toes...etc., and I find the key..,still there.

Now, sadly, some of the panic goes away.

I cross the lit area...as far as I know..unseen. Though, as I gain the tree line, I hear a small group coming on the island.

Then...I get lost.

It is near pitch black and hard to spot the trail up the levee to the far side of the island. I spend ten minutes, naked, lost going back and forth looking for the trail turnoff. I retrace my steps all the way back to he last juncture, and find the trail I should have gone on.

Now I feel stupid, naked, and, closing in on the goal, ready to end this dare, but kind of bummed that it is ending. I always fantasize about being caught, raped, and then I hear the pier.

It is moving. Is it the wind? Can’t tell. It is moving up and down. The metal clang is obvious. Damn...do they see my clothes?

The sound goes on. I think I hear voices.

Well, my heart sinks. I am screwed.

I feel like I have waited forever. Mustering my courage I say fuck it.

My heart is pounding. I am doing the nudie hop.

No one is there and there are my clothes.

I get dressed and as I leave I pass two groups of people. So I wasn’t as alone as I thought.

I wish I had a person to do these with me, and I always am looking for more dares. Hope you liked he story. I have a kik as well, if you want to humiliate my naked flesh.

I love dares where there is no point back once you start, it is how a dare should be, what is the risk if you can hide or just quite. Dares should be something that once you start you are commited and can not get out of until you complete it.

i have done 2, both at a 4 story car park with the top level being rooftop.

one i went to the rooftop and threw my clothes over the edge having to walk through all levels to retrieve them. there was another person in the car park at the time which i did not know prior to starting, after seeing the person i got so scared and tried to avoid best i can. almost certain i wasn't spotted.

another time i took my house keys, a bakpack and a padlock. on the way out of my house i locked the door behind me, leaving the padlock key inside.. went to the rooftop floor and placed the key on the furthest side possible. walked to the bottom floor put my clothes in the bad and padlocked it. leaving me to walk to the rooftop to get house keys, home to get padlock keys, and back to get clothes. this was super scary and i was shaking most of the time. i filmed this task for the person who gave me it though the video is of my walking in the dark most of the time pointing forward so you cant see anything. took me 12 minutes of walking to get my stuff back.

Wow they are really wild dares