Naughtiest Dare

officegirl20

Petite Plaything
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Jun 28, 2025
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What is the naughtiest thing you were dared and chose to or had to do?

About 2 years ago lost a bet i was sure i was going to win. I had to walk about 4 blocks length through central park, wearing just trench coat. All i had on was the coat, 3" wedge sandals and necklaces.
 
Without a doubt a wet shorts contest when I was in my 20's.
It was in front of about 150 people skin to win. I won the contest but it definitely wasn't because I had a hardon.
That many people and a freezing cold ice water bath to start the wetshorts had me in turtle mode.
But it did have its benefits as a woman approached me afterwards to do a photo shoot with her.
 
Not sure if they do it but back when I went to college, somewhere around 1902, streaking was big. Right through the cafeteria. I'm thinking drinking might have been involved??

Wife jumped out naked at an overlook with telescopes looking at the mountains. Place was packed
 
Central Park, you say? Many, many years ago I was there on the grass with a new gf from work, and as we were leaving, a couple of guys complained that we were 'closing the show' and dared us to give better. My gf laughed and nodded for them to follow us. She led us all to a secluded spot in the Ramble, where she had them sit on a rock. She stripped and gave me a bj for their entertainment. Then she went to their rock and gave them a double hand job.
 
Central Park, you say? Many, many years ago I was there on the grass with a new gf from work, and as we were leaving, a couple of guys complained that we were 'closing the show' and dared us to give better. My gf laughed and nodded for them to follow us. She led us all to a secluded spot in the Ramble, where she had them sit on a rock. She stripped and gave me a bj for their entertainment. Then she went to their rock and gave them a double hand job.


Sounds hot. Bet they really enjoyed the show and after
 
What is the naughtiest thing you were dared and chose to or had to do?

About 2 years ago lost a bet i was sure i was going to win. I had to walk about 4 blocks length through central park, wearing just trench coat. All i had on was the coat, 3" wedge sandals and necklaces.
Sounds sexy, but how is it different from walking through the park in a dress, with or without panties?
 
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