Nighttime Outdoor Crossdressing

[kycats]

Looking for crossdressing dares to do at night. They can take place on foot, in my car, at a store, etc. I also like messy, so you could incorporate that. Please make sure to specify the clothes you want me to wear.
I will do dares if they are good and i can do them. You might even be able to convince me to do pics.
Feel free to pm me.

[Silicon]

Well then.
Drive to a secluded place.
Hide your regular clothes in a backpack, lock it with a padlock.
Put on your sluttiest outfit and drive to another secluded spot, at least 1 km away.
Leave the key to the backpacks lock in the car.
Start walking sexy towards the backpack.
When you have found the backpack, start jerking and cum on your face.
For the walk back to the car, take another path.

[kycats]

Thank you! I don't have a bag that can be locked, but i promise I wont cheat on the way back. I'll wait to leave until my famly is asleep. Will report back tomorrow mornibg. If anybody wants to add anything or give me an additional dare, feel free to do so.

[Conviction]

when you do it, wear the shortest skirt you have, no underwear

[kycats]

It's cold here so I'm going to be wearing leggings under my skirt. You can assign a punishment to make up for that.

[ornikiss]

A little dare I love to perform at night, before leaving home dress up completely as a woman (stockings, undies, dress) and on it put some male cloths. Put in a bag a pair of heels you can wear. Go for a little walk, go to wood but before you enter wood, you should not have your male cloths on or standard shoes. Put your male cloths in a more or else visible area (it can be a fence, sidewalk, a little hidden near the road) but it can't be hidden or in wood (I started behind a little fence on the other side of the street giving to wood.

When you enter woods, you can put your heels, you will now walk across woods, path depends on you, the longer, the riskier. When you are at the other side perform a complete slow strip tease throwing you cloths towards the road, it doesn't have to go there (but if you don't throw them far enough, it will be harder to see ;))

Now the hardest, you pick up all your female cloths and put them in your bag and walk/run to where you come from but you can't walk or run if your dick is too small and can't run if not rock hard. When it's cold, rock hard is really hard. when you see the other side, you can finish yourself in woods but you'll have to catch all your sperm in one hands, you can either swallow it or wash your body with it.

Now you'll have to run to pick up your male cloths, dress up back (you can hide in woods there) and come back. If you don't get your cloths back, I hope your female cloths were not too much slutty :D

I have to admit, I prefer perform this in summer as it is warmer but I have perform it at night and risk were really low and always get my cloths back even if my hidden place was on the same fence but well risk gives better orgasm :p

[kycats]

Thank you, will definitely do this. I will probably wait until spring, though. There will also be more people outside then which will make it more fun.

Any more? Im up for messy, wetting, anal, and more.

[kycats]

Ugh. My sister is not going over to her friend's house after all. I can't do the dare tonight, but when I do I'll write about it here.

As usual, feel free to give more dares. I will do them when I can.