Well then use a carrot, should be slim enough, oufit stays the same just start your walk at home. If that doesn't work either, put your hairbrush up your pussy instead of the carrot in the butt...
Is that a dare you dare to do? :)

and how short of a skirt are we thinking?

Im definitely assuming you intend for me to do this at night, im pretty adventurous, but dang lol. Also I go to a community college, so we don't have one, however, my town has a local practice field, does that work?

yes that works and yea you can do it at night

As short as you dare to go :) but i guess it should cover the inserted object :)

Do you own any clothes that you are willing to destroy?
Only need 1 top and 1 bottom, skirt or pants, up to you

yeah, some ratty older jeans, and a tube top I dont midnegetting rid of

So your dare is to drive at least 30 mins away from your house wearing only the ratty jeans and tube top.
When u get to your destination, get out and walk 30 minutes away from your car.
Now using a pair of scissors, cut your clothes from your body into bits that no longer resemble clothes and are useless to cover up with. Then using your vibe, edge 3 times. Then make your way back home. Everytime you stop at lights, you will play with your clit a little. Only when you are safely home may you cum

I would like you to go out in your sexiest lingerie and a coat. With you, you should take a rucksack and a padlock capable of locking said rucksack. Obviously the key should be left at home.
Drive out to the local park and the walk exactly 20 mins away from your car. Now put your coat in the bag and seal it shut. Feeling extra brave? Throw your car keys in there too

ok fine go pee outside- nothing too kinky or risky just a general easy dare!

Well...umm this was really easy as expected lol. I honestly walked out my back door in my robe, and did what was asked..and went back inside lol and that is how you do that.

There are two challenges I created earlier. Here is the first one and I know someone already enjoyed this one:

For this challenge, you require to wear a short shirt or sweater, something that barely reaches your hips. You also need a chain and a lock.

Go to a bench in a park with a chain and a key. Hide the key about 20 meters away from you. Pull the chain through you clothes (through your pants and panties), thus the chain goes in at waist level and gets out a your ankles. Use the lock to connect both ends of the chain, attached to the bench.

Now you will be sitting on the bench with your clothes on. But your pants and panties are locked to the bench. To unlock your clothes, you need the key that is 20 meters away from you. That means you have to strip out of your pants and panties to get the key and return to the bench to retrieve the key.

One restriction, you have to see other people in the park before you are to close the lock. The idea is that you will be forced to wait while your faith is already sealed.

Hope you like this challenge.

This is the kind of dare ive been looking for. This gets me excited just reading it. Thankyou for your post.

The second dare is inspired by some online fiction, this dare is to be done in daylight in a public area....

Item 1:
A throw away t-shirt.
(Or a t-shirt or sweater and a (chain plus) lock. When the keys are home, you can run the chain through the holes and lock it. That way you are unable to wear the item without destroying it or trowing it away.)

Item 2:
You require a throw-away t-shirt or sweater that is a bit tight fitting. Cut two small holes in the tight fitting t-shirt. Your nipples and a good part of your breasts should be exposed, but do not make the hole(s) too large. Part of your breasts should be covered when looking from the side.

Item 3:
A card box with one or two holes in it. When dressed in the shirt with the holes, you should be able to cover your breasts by holding the card box in front of you pressed to your chest. The hole(s) should just be slightly larger then the hole(s) in the tight t-shirt.

The dare:
I imagine you can see where this is going... Anyway, wear item 1 while bringing along item 2 and 3. Travel at least 30 minutes away from your home (or safe place / clothes stack). Find a secluded area like a restroom and throw away or cut item 1.

Now to get home safe you have to wear the shirt with holes that exposes your breasts, while holding the card box to cover your exposed breasts. Have fun walking home and good luck with covering your boobs!

Optional addition 1:
Add some weight in the box to make it harder to carry around. Tape the weight to the box. That way removing the weight might damage the structural integrity of the card box. You can add the weight to the front of the box, thus the box might topple easier and thus making this a bit more daring.

Optional addition 2:
Write in large letters "boobies" or "peep show" at the front of the card box.

Optional addition 3:
Make sure the card box is easily opened at the top. If necessary, cut away part of the flaps.

I hope you like this dare.

Should you this dare I am curious how it goes and if you enjoy it.