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.
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- 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.
- Joined
- Jan 2, 2026
I got dared for a date with my husband, so I had a dress with six buttons. No lingerie. High heels because that's what my husband likes me in. And my bullet vibes against my clit and G-spot... Once the film started, my husband would start the vibes, and every time I edged, I would have to undo one of the buttons...
If (when) the buttons were all undone, I had to take the dress off for the duration of the movie and give my husband a blowjob
It was so scary sitting naked, even on the back row, waiting for the movie to end and the lights to come on before I'd be allowed to cover myself back up...
In the end, I had to use the "out" and use my jacket as a blanket, but that meant leaving the top and bottom button unfastened and going to buy new shoes after the movie, ensuring the sales person saw me not sitting on the hem of my dress and having to open my legs as I fastened the new shoes on to flash my pussy 
If (when) the buttons were all undone, I had to take the dress off for the duration of the movie and give my husband a blowjob
It was so scary sitting naked, even on the back row, waiting for the movie to end and the lights to come on before I'd be allowed to cover myself back up...
In the end, I had to use the "out" and use my jacket as a blanket, but that meant leaving the top and bottom button unfastened and going to buy new shoes after the movie, ensuring the sales person saw me not sitting on the hem of my dress and having to open my legs as I fastened the new shoes on to flash my pussy
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