Best and Worst Dare?

Discussion in 'Temptation Cancun' started by MikeandHeather, Mar 9, 2018.

  1. MikeandHeather

    MikeandHeather I can choose my own title Registered Member

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    The "slingshot" comment in another thread got me thinking (since they are calling for another foot of snow and it is Friday): what is the best and worst dares you have taken and NOT regretted while on vacation? I am sure we can start a regret thread too!
     
  2. Rick

    Rick Addict Registered Member

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    Men in sheer g strings Was a hit — about 6 guys that day!
     
  3. ScubaSteve

    ScubaSteve CCC's The Dude Registered Member

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    I take mostly all my advice from Metallica!

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  4. MikeandHeather

    MikeandHeather I can choose my own title Registered Member

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    Group dares, didn't think about that! Took a dare (sort of) to finish a whole bottle of Don Julio one day.....woke up the next day. Had no regrets because I had no memory.
     
  5. Jen&Kyle

    Jen&Kyle I can choose my own title Registered Member

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    Not sure if this is technically a dare but definitely qualifies as no regrets, is a fun story, fills some time for me as I kill time flying from India to Qatar, plus I am into bottle 2 on this flight and I appreciate a slightly different topic than the norm lately.

    So here goes...
    In our early days of TTR we fell in that category somewhere in the middle. The ‘swayers’ I guess. Maybe closer to vanilla than ls but definitely not vanilla in any terms. Hey if something happens at TTR great, within limits, we go to have fun and if something feels great on vacation then why not.

    So we developed a group of friends over several trips. Lots of flirting. Body shots. AIWC. For the most part it ended there. Slowly but surely the theme changed with one couple. I really got along well with the mrs but again limited to flirting. The guy saying why don’t you two just do it already. Take her to the room followed by a laugh. Blah blah. Over and over. Kind of around the party but after a while you begin to realize this may not just be jokingly around.

    So one crazy long party day she said let’s do it. Rather directly. With my mrs there of course. My mrs saying hell yeah I would love to watch this lol. My mindset going form ha funny... to holy shit this is real, very fast ha. Thinking ok wait is this really ok with him? With her? With my mrs as this was a new frontier. Was it some sort of trap or test? And before you know it yeah it happened. Mrs watching from the corner for a while then taking her turn. I almost treated it like a job (I know better not to now ha) ...got to keep lady #1 and #2 happy. Did I have any regrets? Do I have any regrets? Hell no. Not quite the embarrassing yourself risk of regret type of thing but still fun to share and reminisce. :)
     
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  6. summerbum

    summerbum I can choose my own title Registered Member

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    We got a "bottom exchange" going in a fun hole that resulted in all the guys wearing tiny women's thongs. Suddenly, all of us women became incredibly thirsty, so our guys had to go to the pool bar, wearing our bottoms. Not a pretty sight, but they were great sports!:D
     
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  7. jnine

    jnine I can choose my own title Registered Member

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    OMG that is GREAT! Nicely played ladies!
     
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