My lovely wife Lisa just hit 40 and still looks hot.
Throughout most of her life she has been timid and shying away from showing off her body, let alone do any dares. I've tried but she was too nervous.
I'm not sure what changed recently but when I bought her a new bikini that showed the nipple a little when it was wet, she agreed to try it on and wear it first in the yard. Having fun, she agreed to wear it to the beach that week. There were so many other women with skimpier suits that she didn't feel exposed and was able to relax, even as men stared at her nipples as they walked by.
That night we had the greatest sex.
I know this is not a very revealing dare and not what you are used to but we'd be grateful if you could post this. Who knows where it might lead?