What is the craziest thing you’ve ever done on a dare? Could be a dare from here, from GetDare, from your Dom(me) or partner, or from a friend.
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Craziest thing you’ve ever done on a dare
- Thread starter zeph
- Start date
That would probably be going out in only female clothes. I used scarf to cover most of my face, but still.
I like the thrill that comes from the risk of being seen, but I do not want to be seen. The thought of someone finding out and possible consequences scares me. I was naked outdoors many times, but it was more controlled, than going on 80 minute walk vulnerable like that. It's different to strip in a park at night, when noone is around than going out crossdressed through streets and passing other people, that could possibly stop by and start talking to you.
Ultimately I met almost noone and quite quickly went to a place where it was less likely to meet someone, so after time I felt more confident. Still, it's not something I would easily do again. Before this dare I went out crossdressed once, but it was a bit different. Not all clothes were female, I wore a mask from scream instead of scarf and went just for a short walk, though I passed more people back then - this definitely did not make it easier to do that 80 minute walk. After getting a dare and actually doing it, months have passed. To minimize risk I waited for a moment when I was sure I will be alone at home for the day and at night, so I could easily prepare everything, go out and come back without noone at home noticing. Though with the short walk before I went out when I had people asleep at home.
Sometimes I just have days when I am more daring. This task was one of those that actually require some more willpower to commit and do it. I did some other crazy stuff, but this one is probably the answer for this thread. Big city, noone around knowing I do stuff like this, cameras almost everywhere. Usually I do stuff that makes my avoid people whenever possible. Here I just went out for a walk and until I reached safer place and then home when walking back, I risked stumbling upon someone and them realizing there's a man in those female clothes.
I might do crazier things in the future, as I like to push myself further, but for now, this probably takes the cake.
I like the thrill that comes from the risk of being seen, but I do not want to be seen. The thought of someone finding out and possible consequences scares me. I was naked outdoors many times, but it was more controlled, than going on 80 minute walk vulnerable like that. It's different to strip in a park at night, when noone is around than going out crossdressed through streets and passing other people, that could possibly stop by and start talking to you.
Ultimately I met almost noone and quite quickly went to a place where it was less likely to meet someone, so after time I felt more confident. Still, it's not something I would easily do again. Before this dare I went out crossdressed once, but it was a bit different. Not all clothes were female, I wore a mask from scream instead of scarf and went just for a short walk, though I passed more people back then - this definitely did not make it easier to do that 80 minute walk. After getting a dare and actually doing it, months have passed. To minimize risk I waited for a moment when I was sure I will be alone at home for the day and at night, so I could easily prepare everything, go out and come back without noone at home noticing. Though with the short walk before I went out when I had people asleep at home.
Sometimes I just have days when I am more daring. This task was one of those that actually require some more willpower to commit and do it. I did some other crazy stuff, but this one is probably the answer for this thread. Big city, noone around knowing I do stuff like this, cameras almost everywhere. Usually I do stuff that makes my avoid people whenever possible. Here I just went out for a walk and until I reached safer place and then home when walking back, I risked stumbling upon someone and them realizing there's a man in those female clothes.
I might do crazier things in the future, as I like to push myself further, but for now, this probably takes the cake.
Last edited:
- Joined
- Jan 3, 2026
I went out on a hike on a small trail, left a key at the trail head, then walked in the trail a bit. Once there, I locked my clothes in a bag and went to retrieve the key. Luckily no one showed up, but someone almost did so I had to rush and get dressed just for no one to be there. Either way the mosquitos were very abundant so I had to call it quits before I was their dinner.
- Joined
- Jan 8, 2026
I don't know if it's the craziest thing I've ever done, but it's definitely the craziest thing that's ever happened to me.
I went to a forest and every two minutes I took off an article of clothing (I had spare clothes). When I was naked, I got all my clothes back (except for my pants, which I never found), but I didn't put them on. I sat on a bench and masturbated until I came. When I came, I put on a shirt and my boxers, and a second later a guy came out from behind me and sat on the bench next to me. I was almost certain he had seen me, and it was very dark and late, so without caring that I was only wearing a shirt and boxers, I got up and tried to go to the entrance even though there were people around.
The guy followed me and asked me if I wanted to have sex. Obviously, I said no and left as fast as I could. After walking for a minute or two, making sure he wasn't following me, I sat on a bench outside the forest and put on the rest of my clothes.
I went to a forest and every two minutes I took off an article of clothing (I had spare clothes). When I was naked, I got all my clothes back (except for my pants, which I never found), but I didn't put them on. I sat on a bench and masturbated until I came. When I came, I put on a shirt and my boxers, and a second later a guy came out from behind me and sat on the bench next to me. I was almost certain he had seen me, and it was very dark and late, so without caring that I was only wearing a shirt and boxers, I got up and tried to go to the entrance even though there were people around.
The guy followed me and asked me if I wanted to have sex. Obviously, I said no and left as fast as I could. After walking for a minute or two, making sure he wasn't following me, I sat on a bench outside the forest and put on the rest of my clothes.