Naughtiest Dare

[officegirl20]

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.

 

[Treeview]

On a hot summer day?

 

[officegirl20]

On a hot summer day?

No early evening mid fall

 

[Treeview]

No early evening mid fall

Did you win the bet. How could you lose

 

[officegirl20]

Read my initial post

 

[MaturemanAJ]

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.

 

[Sgts19]

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

 

[Tio_Narratore]

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.

 

[officegirl20]

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

 

[oneoffAkind]

What is the naughtiest thing you were dared and chose to or had to do?

Standing in just my undies in front of the others, I had to wet myself - very hard to do....

 

[hiker283]

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?

 

[officegirl20]

Sounds sexy, but how is it different from walking through the park in a dress, with or without panties?

Guess just the nude under coat kinda different feeling lol

 

[tabber]

Guess just the nude under coat kinda different feeling lol

I bet it was! Even if you were the only one that knew. Anything could have gone wrong...the wind...trip and fall and expose your body. Did it make you all tingly or were you too into the dare? Did your friends that made the bet follow along? Did you have to prove to them you were naked?

 

[athelticguy04]

This sounds like a fun idea

 

[officegirl20]

I bet it was! Even if you were the only one that knew. Anything could have gone wrong...the wind...trip and fall and expose your body. Did it make you all tingly or were you too into the dare? Did your friends that made the bet follow along? Did you have to prove to them you were naked?

Yes tingly and nervous. Walked Alone. Female friend that dropped me off saw nothing under coat before i got out

 

[KyleR215]

I was staying in a hotel and a woman I was chatting on line with came up with this one. I was in a hotel in Norfolk Virginia. I was dared, one time, to strip and leave my room, go to the ice machine and get ice and return. All while completely naked. And I had to video it and send it to her.

 

[tabber]

Yes tingly and nervous. Walked Alone. Female friend that dropped me off saw nothing under coat before i got out

Tell us more about this. Who came up with the dare? How did you feel after it was over? Have you wanted to do it again?

 

[Smoothshavendad]

Yes tingly and nervous. Walked Alone. Female friend that dropped me off saw nothing under coat before i got out

I bet she loved seeing your naked young body!

 

[Viperfixer]

I dared my wife to wear her sheer dress to dinner with nothing underneath. She did it without complaining.

 

[CuriousOneHere]

I dared my wife to lay on the bed in a hotel in a sexy teddy with one boob hanging out and pretend to be asleep when room service was delivered. I had him put it on the table in full sight of my wife. He definitely was looking.

 

[officegirl20]

Tell us more about this. Who came up with the dare? How did you feel after it was over? Have you wanted to do it again?

Friend of mine bet over a sports game. Half excited half nervous.. idk

 

[MamaBitte]

(...) Then she went to their rock and gave them a double hand job.

How did that make you feel? Were you jealous, or did you secretly hope that she would give them more than just a hand job?

 

[tabber]

Friend of mine bet over a sports game. Half excited half nervous.. idk

Did she have to do the same if SHE lost? Who came up with the idea? Hmmm? maybe she DID want to see you naked under the coat. or did you come up with the bet?

 

[Foxed]

Volunteered to get on stage at a live sex show in Amsterdam.

 

[officegirl20]

Did she have to do the same if SHE lost? Who came up with the idea? Hmmm? maybe she DID want to see you naked under the coat. or did you come up with the bet?

Forgot what hers was.. it was different