What is the most embarrassing dare you have done?

It wasn't a dare but a truth. My wife was asked how many men had fucked her before me and she told them the truth. Then I had to tell the truth and admit that she was my first and only lover. It was very embarrassing for me to admit that I had married a very sexually experienced woman and I wasn't experienced at all.

Would be hot to have her tell you some of the stories!! Maybe you guys could role play, you could pretend to be one of her past lovers!!

I was embarrassed when my wife took my dare to wear a thong to sunbathe along the lake shore of our state park. She'd seen a guy do it - I dared her to.
This is OHIO!, not the Riviera!
I assumed she'd go buy a thong bathing suit - but when she stood on the blanket, and unzipped her tight little white short-shorts and tugged them down - I saw that she was wearing one of her thong panties!! She stood there looking around for all the world to enjoy before she finally laid on the blanket and let me put sun lotion on her very pale little bare ass! I saw men taking snaps, and wives punching them!, with their phones and a couple guys moved their boats closer to shore and got out their binoculars!
She wore a short T back up to the car, now that she'd shown the world her very nice little butt, - hips & bare ass swinging ahead of me! I am pretty damn sure the women noticed that those were panties she was wearing!!! The looks they gave her.....and me, as we passed!
Fucked her hard in the car!

That’s awesome!!!!

I was in seventh grade, he was in eighth (we’re both guys). He invited me over to play Atari (yes, I’m old, LOL). At some point, he dared me to pull out my cock. He said if I did, he’d put it in his mouth. But I’d have to do the same to him! I resisted at first, but he kept calling me a pussy! I felt naughty doing it, but finally relented. And when I did, it was hard to deny I wasn’t turned on by it. So there I was getting my first blowjob by the neighbor kid!! Then after a few minutes, he said…OK, my turn! And I held up my end of the bargain!!